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[ CAS No. 206551-41-9 ] {[proInfo.proName]}

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Chemical Structure| 206551-41-9

Chemical Structure| 206551-41-9

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Quality Control of [ 206551-41-9 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 206551-41-9 ]

CAS No. :	206551-41-9	MDL No. :	MFCD09261255
Formula :	C₈H₆BrFO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	-
M.W :	233.03	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 206551-41-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.38
TPSA :	26.3 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.21
Log Po/w (XLOGP3) :	2.51
Log Po/w (WLOGP) :	2.8
Log Po/w (MLOGP) :	3.09
Log Po/w (SILICOS-IT) :	2.79
Consensus Log Po/w :	2.68

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.1
Solubility :	0.183 mg/ml ; 0.000787 mol/l
Class :	Soluble
Log S (Ali) :	-2.71
Solubility :	0.456 mg/ml ; 0.00196 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.61
Solubility :	0.0569 mg/ml ; 0.000244 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.63

Safety of [ 206551-41-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 206551-41-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 206551-41-9 ]
Downstream synthetic route of [ 206551-41-9 ]

[ 206551-41-9 ] Synthesis Path-Upstream 1~1

1
[ 206551-41-9 ]
[ 1195768-19-4 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 3, p. 358 - 362

[ 206551-41-9 ] Synthesis Path-Downstream 1~11

1
[ 206551-41-9 ]
[ 796061-07-9 ]
methyl 9-tosyl-9H-carbazole-1-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 4893 - 4896

2
[ 206551-41-9 ]
[ 478374-74-2 ]

Reference： [1]Patent: EP1394147,2004,A1 .Location in patent: Page 66

3
[ 6165-68-0 ]
[ 206551-41-9 ]
[ 110-71-4 ]
[ 374555-00-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine)palladium (0);	REFERENCE EXAMPLE 83 To a mixture of <strong>[206551-41-9]methyl 3-bromo-2-fluorobenzoate</strong> (117 mg), 2-thiopheneboronic acid (83 mg) and 1,2-dimethoxyethane (2 ml) were added a 2M aqueous solution of sodium carbonate (0.83 ml) and tetrakis(triphenylphosphine)palladium(0) (29 mg) at ambient temperature. The mixture was heated for 3 hours at 90° C. After cooling, the reaction mixture was diluted with ethyl acetate (30 ml), and washed with water (20 ml*3) and brine (20 ml). The organic layer was dried over magnesium sulfate and filtered. After evaporation, the residue was chromatographed on a silica gel eluding with a mixture of ethyl acetate and n-hexane to give methyl 2-fluoro-3-(2-thienyl)benzoate (99 mg). Mass: 237 (m/z, (M+H)+) NMR(DMSO-d6, delta): 3.89 (3H, s), 7.1-7.3 (1H, m), 7.39 (1H, t, J=7.8 Hz), 7.6-7.9 (3H, m), 8.0-8.2 (1H, m).

Reference： [1]Patent: US2003/176454,2003,A1

4
[ 161957-56-8 ]
[ 149-73-5 ]
[ 206551-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In methanol;	EXAMPLE 120 3-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-2-fluoro-benzonitrile A solution of 3-bromo-2-fluorobenzoic acid (0.219 g, 1 mmol) in dry methanol (5 mL) under nitrogen was treated with trimethylorthoformate (0.22 mL, 2 mmol) and p-toluenesulfonic acid (catalytic amount), and then heated under reflux. After 16 h, the mixture was evaporated and the residue partitioned between water and Et2O. the organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated to give methyl 3-bromo-2-fluorobenzoate (0.195 g, 0.84 mmol, 84percent): 1H-NMR (CDCl3) delta7.90-7.85 (m, 1H), 7.71-7.65 (m, 1H), 7.10 (dt, 1H, J=8.0, 1.0 Hz), 3.94 (s, 3H): MS (EI) 232 (M+).
	With toluene-4-sulfonic acid; In methanol;	EXAMPLE 68 2-fluoro-3-(1',2'-Dihydro-2'-oxospiro[cyclohexane-1,3'-[3H]indol-5'-yl)benzaldehyde oxime A solution of 3-bromo-2-fluorobenzoic acid (0.219 g, 1 mmol) in dry methanol (5 ml) under nitrogen was treated with trimethylorthoformate (0.22 ml, 2 mmol) and p-toluenesulfonic acid (catalytic amount), and then heated under reflux. After 16 h, the mixture was evaporated and the residue partitioned between water and Et2O. The organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated to give methyl 3-bromo-2-fluorobenzoate (0.195 g, 0.84 mmol, 84percent): 1H NMR (CDCl3) delta7.90-7.85 (m, 1H), 7.71-7.65 (m, 1H), 7.10 (dt, 1H, J=8.0, 1.0 Hz) and 3.94 (s, 3H): MS (EI) 232 (M+).
	With toluene-4-sulfonic acid; In methanol;	EXAMPLE 120 3-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-2fluoro-benzonitrile A solution of 3-bromo-2-fluorobenzoic acid (0.219 g, 1 mmol) in dry methanol (5 mL) under nitrogen was treated with trimethylorthoformate (0.22 mL, 2 mmol) and p-toluenesulfonic acid (catalytic amount), and then heated under reflux. After 16 h, the mixture was evaporated and the residue partitioned between water and Et2O. the organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated to give methyl 3-bromo-2-fluorobenzoate (0.195 g, 0.84 mmol, 84percent): 1H-NMR (CDCl3) delta7.90-7.85 (m, 1H), 7.71-7.65 (m, 1H), 7.10 (dt, 1H, J=8.0, 1.0 Hz), 3.94 (s, 3H): MS (EI) 232 (M+).

With toluene-4-sulfonic acid; In methanol;

EXAMPLE 68 2-Fluoro-3-(1',2'-dihydro-2'-oxospiro[cyclohexane-1,3'-[3H]indol]-5-yl) A solution of 3-bromo-2-fluorobenzoic acid (0.219 g, 1 mmol) in dry methanol 5 ml) under nitrogen was treated with trimethylorthoformate (0.22 ml, 2 mmol) and p-toluenesulfonic acid (catalytic amount), and then heated under reflux. After 16 h, the mixture was evaporated and the residue partitioned between water and Et2O. The organic layer was washed with sat. sodium hydrogen carbonate solution, water, brine, dried (MgSO4) and evaporated to give methyl 3-bromo-2-fluorobenzoate (0.195 g, 0.84 mmol, 84percent): 1H NMR (CDCl3) delta 7.90-7.85 (m, 1H), 7.71-7.65 (m, 1H), 7.10 (dt, 1H, J=8.0, 1.0 Hz) and 3.94 (s, 3H): MS (EI) 232 (M+).

Reference： [1]Patent: US2002/49204,2002,A1
[2]Patent: US6391907,2002,B1
[3]Patent: US6444668,2002,B1
[4]Patent: US6462032,2002,B1

5
[ 206551-41-9 ]
[ 1129-26-6 ]
3-Bromo-2[-(4-methoxybenzenesulfonyl)amino]-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.037 g (19%)	In N,N-dimethyl-formamide;	EXAMPLE 198 3-Bromo-2[-(4-methoxybenzenesulfonyl)amino]-benzoic acid methyl ester To 0.096 g (0.5 mmol) of 4-methoxyphenylsulphonamide in 3 mL of DMF was added in one portion 0.020 g (0.50 mmol) of 60percent sodium hydride and the reaction was stirre at 25° C. for 15 min. Then, 0.135 g (0.58 mmol) of <strong>[206551-41-9]methyl 3-bromo-2-fluorobenzylate</strong> was added to the solution in one portion and the resulting mixture was heated at 90° C. (bath temperature) for 18 h. The reaction was cooled to room temperature, acidified with 1N HCl and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica eluding with 30percent-50percent ethyl acetate/hexane to provide 0.037 g (19percent) of the desired product. 1 H-NMR(CDCl3): 8 ppm (s, 1H, NH), 6.8-7.8 ppm (m, 7H, Ar), 3.9 ppm (s, 1H, OMe), 3.7 ppm (s, 1H, OMe).
0.037g (19%)	In N,N-dimethyl-formamide;	Example 198 3-Bromo-2[-(4-methoxybenzenesulfonyl)amino]-benzoic acid methyl ester To 0.096g (0.5 mmol) of 4-methoxyphenylsulphonamide in 3mL of DMF was added in one portion 0.020g (0.50 mmol) of 60percent sodium hydride and the reaction was stirred at 25-C for 15 min. Then, 0.135g (0.58 mmol) of <strong>[206551-41-9]methyl 3-bromo-2-fluorobenzylate</strong> was added to the solution in one portion and the resulting mixture was heated at 90 °C (bath temperature) for 18h. The reaction was cooled to room temperature, acidified with 1N HCl and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica eluding with 30percent-50percent ethyl acetate/hexane to provide 0.037g (19percent) of the desired product. 1H-NMR(CDCl3): 8 ppm (s, 1H, NH), 6.8-7.8 ppm (m, 7H, Ar), 3.9 ppm (s, 1H, OMe), 3.7 ppm (s, 1H, OMe).

Reference： [1]Patent: US5929097,1999,A
[2]Patent: EP938471,2001,B1

6
[ 206551-41-9 ]
[ 82702-31-6 ]
[ 77771-03-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium borohydrid;aluminium trichloride; In diethylene glycol dimethyl ether;	EXAMPLE 3 STR11 4-Fluoro-3-bromo-benzyl alcohol from <strong>[206551-41-9]fluorobromobenzoic acid methyl ester</strong>: First 3.8 g (0.1 mole) of sodium borohydride and then 4.5 g (0.033 mole) of aluminum chloride were added in portions to a solution of 23.3 g (0.1 mole) of 4-fluoro-3-bromobenzoic acid methyl ester in 50 ml of diglyme at 5° C. The mixture was subsequently stirred, without cooling, until the exothermic reaction had ended (a rise in temperature up to about 50° C.) and the reaction was then allowed to go to completion in the course of 1 hour at 100° C. The reaction solution was then poured onto a mixture of 125 ml of icewater and 12 ml of concentrated hydrochloric acid and the benzyl alcohol which had separated out was separated off and distilled in vacuo. 18.7 g (91percent of theory) of 4-fluoro-3-bromobenzyl alcohol were obtained in this manner as a colorless oil with a boiling point of 65° to 70° C. (0.1 mbar).

Reference： [1]Patent: US4386035,1983,A

7
[ 1007-16-5 ]
[ 74-88-4 ]
[ 206551-41-9 ]

Yield	Reaction Conditions	Operation in experiment
89.5%	With potassium carbonate; In tert-butyl methyl ether; N,N-dimethyl-formamide; at 20℃; for 16h;	To a 100 mL round bottom flask was added 3-bromo-2-fluorobenzoic acid (5.00 g, 22.8 mmol, Oakwood), potassium carbonate (3.17 g, 22.9 mmol), and DMF (30 mL).Iodomethane, 2 M in MTBE (11.6 ml, 23.2 mmol) was added and the reaction mixture was stirred at RT for 16 hours. The reaction was filtered and the filtrate concentrated was in vacuo. The resulting brown crude residue was taken up with EtOAc and again filtered and concentrated to give methyl 3-bromo-2-fluorobenzoate (4.76 g, 20.4 mmol, 89.5percent yield), as a brown syrup that was used in the Step 2 without further purification.

Reference： [1]Patent: WO2007/61930,2007,A1 .Location in patent: Page/Page column 63

8
[ 67-56-1 ]
[ 161957-56-8 ]
[ 206551-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	sulfuric acid; for 1h;Inert atmosphere; Reflux;	To a 100 mL round bottom flask was added 3-bromo-2-fluorobenzoiotac acid (10 4 g, 10 47 5 mmol), MeOH (100 mL, 2472 mmol) and sulfuric acid (6 mL, 113 mmol) The reaction mixture was refluxed for 1 hr After cooling to rt, the MeOH was removed under reduced pressure and the acidic residue was poured into cold water and EtOAc, the layers were separated and the aqueous layer was extracted with EtOAc The organic layers were combined, washed with brine, dried over sodium sulfate and 15 concentrated under reduced pressure to afford 10 02 g of methyl 3-bromo-2- fluorobenzoate 1H-NMR (400 MHz, DMSO-ds) delta 7 95 (ddd, J = 8 1 , 6 4, and 1 7 Hz, 1 H), 7 82 - 7 87 (m, 1 H), 7 26 (t, J =7 9 Hz, 1 H), and 3 86 (s, 3 H)
	With sulfuric acid; for 1h;Inert atmosphere; Reflux;	To a 100 mL round bottom flask was added 3-bromo-2-fluorobenzoic acid (10.4 g, 47.5 mmol), MeOH (100 mL, 2472 mmol) and sulfuric acid (6 mL, 1 13 mmol). The reaction mixture was refluxed for 1 hr. After cooling to rt, the MeOH was removed under reduced pressure and the acidic residue was poured into cold water and EtOAc, the layers were separated and the aqueous layer was extracted with EtOAc. The organic layers were combined, washed with brine, dried over NaSO and concentrated under reduced pressure to afford methyl 3-bromo-2-fluorobenzoate. 10.02 g. 1H-NMR (400 MHz, DMSO-de) delta 7.95 (ddd, J = 8.1 , 6.4, and 1 .7 Hz, 1 H), 7.82 - 7.87 (m, 1 H), 7.26 (t, J =7.9 Hz, 1 H), and 3.86 (s, 3 H).
	With sulfuric acid; at 20℃; for 18h;	3-Bromo-2-fluorobenzoic acid was transformed to intermediate 4 using the same procedure reported in example intermediate 2 to afford the corresponding amine as pale yellow oil.

With sulfuric acid; for 1h;Reflux;

Intermediate 15: N-{3-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide; Step A: Methyl 3-bromo-2-fluorobenzoate; To a 100 mL round bottom flask was added 3-bromo-2-fluorobenzoic acid (10.4 g, 47.5 mmol), MeOH (100 mL, 2472 mmol) and sulfuric acid (6 mL, 113 mmol). The reaction mixture was refluxed for 1 hr. After cooling to rt, the MeOH was removed under reduced pressure and the acidic residue was poured into cold water and EtOAc, the layers were separated and the aqueous layer was extracted with EtOAc. The organic layers were combined, washed with brine, dried over NaSO4 and concentrated under reduced pressure to afford 10.02 g of methyl 3-bromo-2-fluorobenzoate. 1H-NMR (400 MHz, DMSO-d6) delta 7.95 (ddd, J=8.1, 6.4, and 1.7 Hz, 1H), 7.82-7.87 (m, 1H), 7.26 (t, J=7.9 Hz, 1H), and 3.86 (s, 3H).

Reference： [1]Patent: WO2010/104899,2010,A1 .Location in patent: Page/Page column 162
[2]Patent: WO2011/59610,2011,A1 .Location in patent: Page/Page column 86
[3]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 358 - 362
[4]Patent: US9126993,2015,B2 .Location in patent: Page/Page column 51
[5]Patent: US2009/298815,2009,A1 .Location in patent: Page/Page column 52-53

9
[ 206551-41-9 ]
[ 4248-19-5 ]
[ 1042055-86-6 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 90℃;Inert atmosphere; Sealed flask;	In a 500 mL flask was placed 1 ,1-diotamethylethyl carbamate (6 03 g, 51 5 mmol), <strong>[206551-41-9]methyl 3-bromo-2-fluorobenzoate</strong> (10 g, 42 9 mmol), Pd2(dba)3 CHCI3 (0 89 g, 0 86 mmol), xantphos (1 49 g, 2 57 mmol) and cesium carbonate (16 8 g, 51 5 mmol) The flask was sealed with a rubber septum, placed under high vac, and toluene (200 mL) was added Three cycles of high vac/N2 were performed and the reaction 25 mixture was stirred at 90 C overnight The reaction was filtered through a pad of celite with EtOAc washing and concentrated To the residue was added DCM (200 mL) followed by TFA (50 mL, 649 mmol), and the mixture was stirred at rt for 1 h The volatiles were removed under reduced pressure and the residue was taken up in EtOAc and washed with saturated NaHCO3 and brine The organic layer was dried over sodium sulfate and stripped onto silica and column chromatographed on silica with 5% to 50% EtOAc Hexane to give 5 53 g (76%) of the title compound of Step B 1H-NMR (400 MHz, DMSO-d6) delta 6 92 - 7 01 (m, 3 H), 5 37 (s, 2 H), and 3 81 (s, 3 H) MS (ESI) 170 [M+H]+
	With caesium carbonate;tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 90℃;Inert atmosphere;	Step B: Methyl 3-amino-2-fluorobenzoate; In a 500 mL flask was placed 1,1-dimethylethyl carbamate (6.03 g, 51.5 mmol), <strong>[206551-41-9]methyl 3-bromo-2-fluorobenzoate</strong> (10 g, 42.9 mmol), Pd2(dba)3.CHCl3 (0.89 g, 0.86 mmol), xantphos (1.49 g, 2.57 mmol) and cesium carbonate (16.8 g, 51.5 mmol). The flask was sealed with a rubber septum, placed under high vacuum, and toluene (200 mL) was added. Three cycles of high vacuum/N2 were performed and the reaction mixture was stirred at 90 C. overnight. The reaction was filtered through a pad of celite with EtOAc washing and concentrated. To the residue was added DCM (200 mL) followed by TFA (50 mL, 649 mmol), and the mixture was stirred at rt for 1 h. The volatiles were removed under reduced pressure and the residue was taken up in EtOAc and washed with saturated NaHCO3 and brine. The organic layer was dried over NaSO4, stripped onto silica and column chromatographed on silica with 5% to 50% EtOAc:Hexane to give 5.53 g (76%) of the title compound of Step B. 1H-NMR (400 MHz, DMSO-d6) delta 6.92-7.01 (m, 3H), 5.37 (s, 2H), and 3.81 (s, 3H). MS (ESI): 170 [M+H]+.

Reference： [1]Patent: WO2010/104899,2010,A1 .Location in patent: Page/Page column 162-163
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 358 - 362
[3]Patent: US2009/298815,2009,A1 .Location in patent: Page/Page column 53

10
[ 206551-41-9 ]
[ 114995-47-0 ]
[ 333793-52-5 ]

Yield	Reaction Conditions	Operation in experiment
60.9%		To a solution of N-(4fluorophenyl)-2,2-dimethylpropionamide (195 mg) in tetrahydrofuran (2 ml) was added a solution of n-butyl lithium in n-hexane (1.54M, 1.5 ml) dropwise at 0° C. under nitrogen atmosphere, and the mixture was stirred for 2 hours at 0° C. To the reaction mixture was added triisopropyl borate (0.692 ml) at -40° C., and the mixture was stirred for 30 minutes at ambient temperature.. To the mixture was added 1N-hydrochloric acid (3 ml), and the mixture was diluted with ethyl acetate and water.. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure.. To the residue were added <strong>[206551-41-9]methyl 3-bromo-2-fluorobenzoate</strong> (117 mg), tetrakis(triphenylphosphine)palladium (29 mg), an aqueous solution of sodium carbonate (2M, 2 ml) and 1,2-dimethoxyethane (5 ml).. The resulting mixture was stirred under nitrogen atmosphere for 48 hours at 75° C., and diluted with ethyl acetate and water.. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure.. The residue was purified with a silica gel column chromatography eluding with 20percent ethyl acetate/n-hexane to give 2'-(2,2-dimethylpropionamido)-2,5'-difluoro-biphenyl-3-carboxylic acid methyl ester (106 mg, 60.9percent). APCI-mass m/z: 348 (M+1) NMR (DMSO-d6, delta); 0.96 (9H, s), 3.85 (3H, s), 7.2-7.4 (4H, m), 7.52 (1H, dt, J=2.0 Hz, 7.1 Hz), 7.86 (1H, dt, J=1.9 Hz, 7.3 Hz), 8.92 (1H, s).

Reference： [1]Patent: US6770667,2004,B1 .Location in patent: Page column 20

11
[ 206551-41-9 ]
[ 17997-47-6 ]
[ 76-05-1 ]
methyl 2-fluoro-3-(pyridine-2-yl)benzoate trifluoroacetate [ No CAS ]
[ 939024-44-9 ]

Yield	Reaction Conditions	Operation in experiment
17%; 23%		In a 150 mL round bottom flask was combined methyl 3-brorno-2-fluorobenzoate (1.47 g,6.3 mmol), DMF (10 mL), silver oxide (0.79 g, 6.4 mmol), 2-(tributylstannyl)pyridine (2.40 ml, 7.2 mmol), and dichlorobis(triphenylphosphine)-palladium (II) (0.23 g, 0.33 mmol) and the mixture was stirred at 100 0C fo about 72 h. Monitoring the reaction by LC-MS revealed two products, the ester and the hydrolyzed product. The reaction was cooled, filtered through a pad of celite and the celite was washed with EtOAc. The filtrate was concentrated in vacuo and taken up in a small amount of DMF. The solution was purified by reverse-phase preparative HPLC on a Phenomenex Luna column (10 micron, <n="66"/>A-1050-WO-PCT - 64 -C18, 100 A, 150 x 50 mm) eluting at 45 ml/min with an linear gradient of 10percent(v/v) to 100percent MeCN (0.1percent v/v TFA) in water (0.1percent TFA) over 10 minutes to give 2-fluoro-3- (pyridine-2-yl)benzoic acid (0.24 g, 0.72 mmol, 23percent yield) as a light red-colored TFA salt and methyl 2-fluoro-3-(pyridine-2-yl)benzoate (0.19 g, 0.55 mmol, 17percent yield) as a golden syrup-colored TFA salt.

Reference： [1]Patent: WO2007/61930,2007,A1 .Location in patent: Page/Page column 63-64

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Alkylbenzene ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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