[ CAS No. 186590-01-2 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 186590-01-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 186590-01-2 ]

SDS Specification

Alternatived Products of [ 186590-01-2 ]

Product Details of [ 186590-01-2 ]

CAS No. :	186590-01-2	MDL No. :	MFCD13185487
Formula :	C₇H₄FNO	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	ZAYFMRICIYQIAP-UHFFFAOYSA-N
M.W :	137.11	Pubchem ID :	11029901
Synonyms :

Calculated chemistry of [ 186590-01-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.14
TPSA :	44.02 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	1.94
Log Po/w (WLOGP) :	1.82
Log Po/w (MLOGP) :	1.22
Log Po/w (SILICOS-IT) :	1.74
Consensus Log Po/w :	1.63

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.36
Solubility :	0.604 mg/ml ; 0.0044 mol/l
Class :	Soluble
Log S (Ali) :	-2.49
Solubility :	0.445 mg/ml ; 0.00325 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.16
Solubility :	0.955 mg/ml ; 0.00697 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 186590-01-2 ]

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

Application In Synthesis of [ 186590-01-2 ]

* 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 [ 186590-01-2 ]
Downstream synthetic route of [ 186590-01-2 ]

[ 186590-01-2 ] Synthesis Path-Upstream 1~1

1
[ 191014-55-8 ]
[ 186590-01-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With aluminum (III) chloride In toluene at 130℃; for 18 h;	A mixture of intermediate 127, 4-fluoro-2-methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 C. for 18 hrs. After cooling, ice water (~50 mL) was added and the resulting mixture extracted with ether (20 mLx2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95percent) as a white solid: 1H NMR (DMSO-d6, 300 MHz) ? ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H), 11.64 (1H, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) ? ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35. HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199.
95%	Stage #1: With aluminum (III) chloride In toluene at 130℃; for 18 h; Stage #2: With water In toluene	A mixture of 4-fluoro-2-methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl₃(5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130° C. for 18 hrs. After cooling, ice water (50 mL)was added and the resulting mixture extracted with ether (20 mL.x.2). The combined extracts were washed sequentially with water and brine, then dried (MgSO₄), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95percent) as a white solid: ¹H NMR (DMSO-d6, 300 MHz) δ ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H), 11.64 (1H, s, OH); ¹³C NMR (DMSO-d6, 75.5 Hz) δ ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84,161.41, 161.58, 163.00, 166.35. HRMS (ESI-) calcd for C₇H₃NOF (M-H) 136.0199, found 136.0199.
95%	Stage #1: With aluminum (III) chloride In toluene at 130℃; for 18 h; Stage #2: With water In toluene at 0℃;	4-Fluoro-2-hydroxyben.sum.onitrile. A mixture of intermediate 127, 4-fluoro-2- methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl₃ (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 °C for 18 hrs. After cooling, ice water (~50 mL)was added and the resulting mixture extracted with ether (20 mL x 2). The combined extracts were washed sequentially with water and brine, then dried (MgSO₄), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95percent) as a white solid: ¹H NMR (DMSO-d6, 300 MHz) δ ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (IH, dd, J = 7 Hz, J = 8.5 Hz, Ar-H), 11.64 (IH, s, OH); ¹³C NMR (DMSO-d6, 75.5 Hz) δ ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35.HRMS (ESI-) calcd for C₇H₃NOF (M-H) 136.0199, found 136.0199.

Reference： [1] Patent: US2005/267105, 2005, A1, . Location in patent: Page/Page column 67
[2] Patent: US2007/111984, 2007, A1, . Location in patent: Page/Page column 33
[3] Patent: WO2007/64316, 2007, A1, . Location in patent: Page/Page column 153
[4] Patent: WO2007/39172, 2007, A1, . Location in patent: Page/Page column 157-158
[5] Patent: US2008/261979, 2008, A1, . Location in patent: Page/Page column 74

[ 186590-01-2 ] Synthesis Path-Downstream 1~13

1
[ 79-44-7 ]
[ 186590-01-2 ]
[ 870562-93-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With triethylamine; In 1,2-dichloro-ethane; for 20h;Heating / reflux;	Under N2, a stirred solution of intermediate 129, <strong>[186590-01-2]4-fluoro-2-hydroxybenzonitrile</strong> (685 mg, 5.00 mmol), dimethylcarbamoyl chloride, and triethylamine (606 mg, 6 mmol) in dichloroethane (10 mL) was heated at reflux for 20 hrs. The cooled mixture was diluted with dichloroethane (10 mL) washed with water, and brine. The organic layer was separated, dried (Na2SO4), concentrated, and the residue purified by column chromatography (SiO2, 5% ethyl acetate-CH2Cl2) to provide 700 mg (Yield 67%) of the title compound as a white crystalline solid: 1H NMR (CDCl3, 500 MHz) ? ppm: 3.03 (3H, s, NMe), 3.15 (3H, s, NMe), 6.99 (1H, dt, J=2.5 Hz, 8.5 Hz, Ar-H), 7.23 (1H, dd, J=2.5 Hz, 9.5 Hz, Ar-H), 7.61 (1H, dd, J=9 Hz, 6 Hz, Ar-H); 13C NMR (CDCl3, 125.77 Hz) ? ppm: 36.76, 37.06, 102.84, 102.86, 111.59, 111.79, 113.24, 113.42, 114.99, 134.36, 134.45, 152.54, 155.06, 155.16, 164.26, 166.31. HRMS (ESI) calcd for C10H10N2O2F (M+H) 209.0726, found 209.0722.
67%	With triethylamine; In dichloromethane; for 20h;Heating / reflux;	Under N2, a stirred solution of <strong>[186590-01-2]4-fluoro-2-hydroxybenzonitrile</strong> (685 mg, 5.00 mmol), dimethylcarbamoyl chloride, and triethylamine (606 mg, 6 mmol) in dichloromethane (10 mL) was heated at reflux for 20 hrs. The cooled mixture was diluted with dichloromethane (10 mL) washed with water, and brine. The organic layer was separated, dried (Na2SO4), concentrated, and the residue purified by column chromatography (SiO2, 5% ethyl acetate-CH2Cl2) to provide 700 mg (Yield 67%) of the title compound as a white crystalline solid: 1H NMR (CDCl3, 500 MHz) delta ppm: 3.03 (3H, s, NMe), 3.15 (3H, s, NMe), 6.99 (1H, dt, J=2.5 Hz, 8.5 Hz, Ar-H), 7.23 (1H, dd, J=2.5 Hz, 9.5 Hz, Ar-H), 7.61 (1H, dd, J=9 Hz, 6 Hz, Ar-H); 13C NMR (CDCl3, 125.77 Hz) delta ppm: 36.76, 37.06, 102.84, 102.86, 111.59, 111.79, 113.24, 113.42, 114.99, 134.36, 134.45, 152.54, 155.06, 155.16, 164.26, 166.31. HRMS (ESI) calcd for C10H10N2O2F (M+H) 209.0726, found 209.0722.
67%	With triethylamine; In 1,1-dichloroethane; for 20h;Heating / reflux;	Dimethyl-carbamic acid 2-cyano-5-fluoro-phenyl ester. Under N2, a stirred solution of intermediate 129, <strong>[186590-01-2]4-fluoro-2-hydroxybenzonitrile</strong> (685 mg, 5.00 mmol), dimethylcarbamoyl chloride, and triethylamine (606 mg, 6 mmol) in dichloroethane (10 mL) was heated at reflux for 20 hrs. The cooled mixture was diluted with dichloroethane (10 mL) washed with water, and brine. The organic layer was separated, dried (Na2SO4), concentrated, and the residue purified by column chromatography (SiO2, 5% ethyl acetate-CH2Cl2) to provide 700 mg (Yield 67%) of the title compound as a white crystalline solid: 1H NMR (CDCl3, 500 MHz) delta ppm: 3.03 (3H, s, NMe), 3.15 (3H, s, NMe), 6.99 (1H, dt, J=2.5 Hz, 8.5 Hz, Ar-H), 7.23 (1H, dd, J=2.5 Hz, 9.5 Hz, Ar-H), 7.61 (1H, dd, J=9 Hz, 6 Hz, Ar-H); 13C NMR (CDCl3, 125.77 Hz) delta ppm: 36.76, 37.06, 102.84, 102.86, 111.59, 111.79, 113.24, 113.42, 114.99, 134.36, 134.45, 152.54, 155.06, 155.16, 164.26, 166.31. HRMS (ESI) calcd for C10H10N2O2F (M+H) 209.0726. found 209.0722.

67%

With triethylamine; In 1,1-dichloroethane; for 20h;Heating / reflux;

Dimethyl-carbamic acid 2-cyano-5-fluoro-phenyl ester. Under N2, a stirred solution of intermediate 129, <strong>[186590-01-2]4-fluoro-2-hydroxybenzonitrile</strong> (685 mg, 5.00 mmol), dirnethylcarbamoyl chloride, and triethylamine (606 mg, 6 mmol) in dichloroethane (10 mL) was heated at reflux for 20 hrs. The cooled mixture was diluted with dichloroethane (10 mL) washed with water, and brine. The organic layer was separated, dried (Na2SO4), concentrated, and the residue purified by column chromatography (SiO2, 5% ethyl acetate-CH2Cl2) to provide 700 mg (Yield 67%) of the title compound as a white crystalline solid: 1H NMR (CDCl3, 500 MHz) delta ppm: 3.03 (3H, s, NMe), 3.15 (3H, s, NMe), 6.99 (IH, dt, J = 2.5 Hz, 8.5 Hz, Ar-H), 7.23 (IH, dd, J = 2.5 Hz, 9.5 Hz, Ar-H), 7.61 (IH, dd, J = 9 Hz, 6 Hz, Ar-H); 13C NMR <n="157"/>(CDCl3, 125.77 Hz) delta ppm: 36.76, 37.06, 102.84, 102.86, 111.59, 111.79, 113.24, 113.42, 114.99, 134.36, 134.45, 152.54, 155.06, 155.16, 164.26, 166.31. HRMS (ESI) calcd for C10H10N2O2F (M+H) 209.0726, found 209.0722.

Reference： [1]Patent: US2005/267105,2005,A1 .Location in patent: Page/Page column 68
[2]Patent: US2007/111984,2007,A1 .Location in patent: Page/Page column 34
[3]Patent: US2007/129379,2007,A1 .Location in patent: Page/Page column 27
[4]Patent: WO2007/64316,2007,A1 .Location in patent: Page/Page column 155-156

2
[ 191014-55-8 ]
[ 186590-01-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With aluminum (III) chloride; In toluene; at 130℃; for 18h;	A mixture of intermediate 127, 4-fluoro-2-methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 C. for 18 hrs. After cooling, ice water (~50 mL) was added and the resulting mixture extracted with ether (20 mLx2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) ? ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H), 11.64 (1H, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) ? ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35. HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199.
95%		A mixture of 4-fluoro-2-methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 C. for 18 hrs. After cooling, ice water (50 mL)was added and the resulting mixture extracted with ether (20 mL×2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) delta ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H), 11.64 (1H, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) delta ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84,161.41, 161.58, 163.00, 166.35. HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199.
95%		4-Fluoro-2-hydroxyben?onitrile. A mixture of intermediate 127, 4-fluoro-2- methoxybenzonitrile, (4.53 g, 30 mmol;) and AlCl3 (5.0 g, 37.6 mmol; Aldrich) in anhydrous toluene (30 mL) was stirred at approximately 130 C for 18 hrs. After cooling, ice water (~50 mL)was added and the resulting mixture extracted with ether (20 mL x 2). The combined extracts were washed sequentially with water and brine, then dried (MgSO4), and concentrated in vacuo to provide the title compound (3.90 g, 28.5 mmol, Yield 95%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) delta ppm: 6.74-6.84 (2H, m, Ar-Hs), 7.71 (IH, dd, J = 7 Hz, J = 8.5 Hz, Ar-H), 11.64 (IH, s, OH); 13C NMR (DMSO-d6, 75.5 Hz) delta ppm: 95.13 102.45, 102.78, 106.53, 106.83 115.53, 134.68, 134.84, 161.41, 161.58, 163.00, 166.35.HRMS (ESI-) calcd for C7H3NOF (M-H) 136.0199, found 136.0199.

		To a solution of 1 g of 4-fluoro-2-methoxy-benzonitrile in 15 ml_ of dichloroethane was added 1.1 g of aluminium trichloride. The resulting mixture was refluxed for 1 day then poured slowly into water and extracted with ethyl acetate. The organic extracts were washed twice with 10% aqueous solution of sodium hydroxide. The combined basic layers were washed twice with ethyl acetate, acidified with concentrated aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic extracts were washed with water, with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 0.78 g of 4-fluoro-2- hydroxy-benzonitrile as a white solid. C7H4FNO (137.11), MS(ESI): 138.17 (M+H+).
		To a solution of 1 g of 4-fluoro-2-methoxy-benzonitrile in 15 mL of dichloroethane was added 1.1 g of aluminum trichloride. The resulting mixture was refluxed for 1 day then poured slowly into water and extracted with ethyl acetate. The organic extracts were washed twice with 10% aqueous solution of sodium hydroxide. The combined basic layers were washed twice with ethyl acetate, acidified with concentrated aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic extracts were washed with water, with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 0.78 g of 4-fluoro-2-hydroxy-benzonitrile as a white solid.C7H4FNO (137.11), MS (ESI): 138.17 (M+H+).

Reference： [1]Patent: US2005/267105,2005,A1 .Location in patent: Page/Page column 67
[2]Patent: US2007/111984,2007,A1 .Location in patent: Page/Page column 33
[3]Patent: WO2007/64316,2007,A1 .Location in patent: Page/Page column 153
[4]Patent: WO2007/39172,2007,A1 .Location in patent: Page/Page column 157-158
[5]Patent: US2008/261979,2008,A1 .Location in patent: Page/Page column 74

4
[ 1514-87-0 ]
[ 186590-01-2 ]
[ 933772-76-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ISOPROPYLAMIDE; at 110℃; for 3h;	To a solution of 4.6 g of <strong>[186590-01-2]4-fluoro-2-hydroxy-benzonitrile</strong> in 15 ml_ of anhydrous dimethylacetamide were added 6.8 g of methyl chlorodifluororacetate and 6.5 g of potassium carbonate. The resulting mixture was degassed by bubbling argon through it and heated to 1100C for 2h then an additional 6.5 g of methyl chlorodifluororacetate and 6.5 g of potassium carbonate were added. The resulting mixture was heated to 11O0C for another hour then concentrated under reduced pressure. The residue was taken into ethyl acetate, washed twice with a molar aqueous solution of sodium hydroxide, with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient from heptane 100 to heptane 80/ ehtyl acetate 20) to give 4.78 g of 2-difluoromethoxy-4-fluoro-benzonitrile as a yellowish liquid. C8H4F3NO (187.12), MS(ESI): 188.0 (M+H+).
	With potassium carbonate; In ISOPROPYLAMIDE; at 110℃; for 3h;	To a solution of 4.6 g of <strong>[186590-01-2]4-fluoro-2-hydroxy-benzonitrile</strong> in 15 mL of anhydrous dimethylacetamide were added 6.8 g of methyl chlorodifluororacetate and 6.5 g of potassium carbonate. The resulting mixture was degassed by bubbling argon through it and heated to 110 C. for 2 h then an additional 6.5 g of methyl chlorodifluororacetate and 6.5 g of potassium carbonate were added. The resulting mixture was heated to 110 C. for another hour then concentrated under reduced pressure. The residue was taken into ethyl acetate, washed twice with a molar aqueous solution of sodium hydroxide, with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient from heptane 100 to heptane 80/ethyl acetate 20) to give 4.78 g of 2-difluoromethoxy-4-fluoro-benzonitrile as a yellowish liquid.C8H4F3NO (187.12), MS (ESI): 188.0 (M+H+).

Reference： [1]Patent: WO2007/39172,2007,A1 .Location in patent: Page/Page column 157-158
[2]Patent: US2008/261979,2008,A1 .Location in patent: Page/Page column 74

5
[ 186590-01-2 ]
2-hydroxy-4-fluoro-benzylamine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; water; ethyl acetate; under 3102.97 Torr; for 96h;	2-Hydroxy-4-fluoro-benzylamine hydrochloride. A solution of intermediate 134, 2-(benzyloxy)-4-fluorobenzonitrile, (9.03 g, 39.7 mmol) in ethanol (100 mL) and ethyl acetate (100 mL) was stirred with 10% palladium on carbon (1.67 g) and concentrated hydrochloric acid (12 mL, 144 mmol) under a hydrogen atmosphere (60 psi) for four days. The catalyst was removed by filtration through Celite, and the filtrate was concentrated. The crude product was triturated with ether and the resulting solid collected by filtration to give the title compound (5.24 g, 74% yield) as a pale orange solid. 1H NMR (500 MHz, DMSO-D6) delta ppm: 10.81 (1H, s), 8.18 (3H, s), 7.36 (1H, t, J=17.3 Hz), 6.79 (1H, dd, J=10.8, 2.6 Hz), 6.66 (1H, dt, J=8.5, 2.3 Hz), 3.90 (2H, d, J=5.2 Hz).

Reference： [1]Patent: US2007/129379,2007,A1 .Location in patent: Page/Page column 28

6
[ 1440-61-5 ]
[ 186590-01-2 ]
[ 870562-91-7 ]

Yield	Reaction Conditions	Operation in experiment
83%		4-Fluoro-2-(2-morpholino-2-oxoethoxy)benzonitrile. To a solution of intermediate 129, <strong>[186590-01-2]4-fluoro-2-hydroxybenzonitrile</strong>, (685 mg, 5 mmol) in dimethylformamide (8 mL, Sure Seal; Aldrich) was added NaH (200 mg, 5 mmol; 60% oil dispersion; Aldrich), and the mixture stirred for 5 min under an anhydrous nitrogen atmosphere. To this was added 4-(2-chloroacetyl)morpholine (900 mg, 5.5 mmol, 1.1 eq.; Avocado Organics), and stirring continued at room temperature for 21 hrs. The reaction was quenched by careful addition of water (30 mL). The resulting mixture was extracted with CH2Cl2 (25 mL×2). The combined extracts were washed with brine, dried (MgSO4) and concentrated. The residue was triturated to obtain 1.10 g (4.17 mmol, Yield 83%) of the title compound as a white solid: 1H NMR (CDCl3, 500 MHz) delta ppm: 3.63 (2H, t, J=4 Hz, NCH2), 3.67 (1H, m, OCH), 3.72 (1H, m, OCR), 4.86 (2H, s, OCH2), 6.80-6.86 (2H, m, Ar-Hs), 7.61 (1H, dd, J=8.5 Hz, 6.1 Hz, Ar-H); 13C NMR (CDCl3, 125.77 Hz) delta ppm: 42.63, 46.04, 66.80, 68.33, 98.45, 98.47, 101.57, 101.79, 109.56, 109.74, 115.42, 135.48, 135.57, 161.26, 161.35, 114.79, 165.23, 167.28. HRMS calcd for C13H14N2O3F (M+H) 265.0988. found 265.0998.
83%		4-Fluoro-2-(2-morpholino-2-oxoethoxy)benzonitrile. To a solution of intermediate 129, <strong>[186590-01-2]4-fluoro-2-hydroxybenzonitrile</strong>, (685 mg, 5 mmol) in dimethylformamide (8 mL, Sure Seal; Aldrich) was added NaH (200 mg, 5 mmol; 60% oil dispersion; Aldrich), and the mixture stirred for 5 min under an anhydrous nitrogen atmosphere. To this was added 4-(2-chloroacetyl)morpholine (900 mg, 5.5 mmol, 1.1 eq.; Avocado Organics), and stirring continued at room temperature for 21 hrs. The reaction was quenched by careful addition of water (30 mL). The resulting mixture was extracted with CH2Cl2 (25 mLx2). The combined extracts were washed with brine, dried (MgSO4) and concentrated. The residue was triturated to obtain 1.10 g (4.17 mmol, Yield 83%) of the title compound as a white solid: 1H NMR (CDCl3, 500 MHz) 5 ppm: 3.63 (2H, t, J = 4 Hz, NCH2), 3.67 (IH, m, OCH), 3.72 (IH, m, OCH), 4.86 (2H, s, OCH2), 6.80-6.86 (2H, m, Ar-Hs), 7.61 (IH, dd, J = 8.5 Hz, 6.1 Hz, Ar-H); 13C NMR (CDCl3, 125.77 Hz) delta ppm: 42.63, 46.04, 66.80, 68.33, 98.45, 98.47, 101.57, 101.79, 109.56, 109.74, 115.42, 135.48, 135.57, 161.26, 161.35, 114.79, 165.23, 167.28. HRMS calcd for C13H14N2O3F (M+H) 265.0988, found 265.0998.

Reference： [1]Patent: US2007/129379,2007,A1 .Location in patent: Page/Page column 26
[2]Patent: WO2007/64316,2007,A1 .Location in patent: Page/Page column 154

7
[ 113826-06-5 ]
[ 186590-01-2 ]
[ 1323276-82-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 650 - 655

8
[ 186590-01-2 ]
[ 1323276-31-8 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 650 - 655

9
[ 105-36-2 ]
[ 186590-01-2 ]
ethyl 3-amino-6-fluorobenzofuran-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate; In acetone; at 40℃; for 12h;	To an 8 ml. vial <strong>[186590-01-2]4-fluoro-2-hydroxybenzonitrile</strong> (150 mg, 1.094 mmol) was dissolved in acetone (2188 .iL). To the solution was added ethyl 2-bromoacetate (121 tL, 1.094 mmol) followed by potassium carbonate (151 mg, 1.094 mmol). The vial was sealed with electricaltape and heated to 40 C for 12 h. The reaction was allowed to cool to room temperature and water (2 mL) and EtOAc (2 mL) were added. The organic layer was separated and the aqueous layer was washed with EtOAc (2 x 2 mL). The combined organic layer was dried over MgSO4 and concentrated. The cmde reaction mixture was purified by silica gel chromatography (80:20 HexIEtOAc). The desired product, ethyl 3-amino-6-fluorobenzofuran-2-carboxylate, was obtained as a white solid (186 mg, 76% yield).
76%	With potassium carbonate; In acetone; at 40℃; for 12h;Sealed tube;	To an 8 mL vial <strong>[186590-01-2]4-fluoro-2-hydroxybenzonitrile</strong> (150 mg, 1.094 mmol) was dissolved in acetone (2188 L). To the solution was added ethyl 2-bromoacetate (121 L, 1.094 mmol) followed by potassium carbonate (151 mg, 1.094 mmol). The vial was sealed with electrical tape and heated to 40 C for 12 h. The reaction was allowed to cool to room temperature and water (2 mL) and EtOAc (2 mL) were added. The organic layer was separated and the aqueous layer was washed with EtOAc (2 x 2 mL). The combined organic layer was dried over MgSO4 and concentrated. The crude reaction mixture was purified by silica gel chromatography (80:20 Hex/EtOAc). The desired product, ethyl 3-amino-6-fluorobenzofuran- 2-carboxylate , was obtained as a white solid (186 mg, 76% yield).

Reference： [1]Patent: WO2017/15449,2017,A1 .Location in patent: Page/Page column 362
[2]Patent: WO2019/67864,2019,A1 .Location in patent: Page/Page column 328

10
[ 75-03-6 ]
[ 186590-01-2 ]
[ 1255870-63-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate; In N,N-dimethyl-formamide;	<strong>[186590-01-2]4-fluoro-2-hydroxybenzonitrile</strong> (50 mg, 0.32 mmol) and DMF (2 ml) were put in a round-bottom flask and stirred, finely ground potassium carbonate (133 mg, 0.96 mmol) was added thereto, and then iodoethane (0.03 ml, 0.39 mmol) was added thereto, followed by stirring. After confirming by TLC that the base compound had disappeared, DMF was vacuum-distilled, and the residue was diluted with ethyl acetate and then washed with brine. The residue obtained after vacuum distillation was subjected to column chromatography (hexane:ethyl acetate=5:1) to obtain 2-ethoxy-4-bromo-benzonitrile (53.8 mg). (Yield: 94%)

Reference： [1]Patent: US2018/265462,2018,A1 .Location in patent: Paragraph 0151

11
[ 186590-01-2 ]
methyl 3‐[4‐(2‐cyano‐5‐fluorophenoxymethyl)phenyl]propanoate [ No CAS ]

Reference： [1]Patent: CN109988065,2019,A

12
[ 186590-01-2 ]
3‐[4‐(2‐cyano‐5‐fluorophenoxymethyl)phenyl]propanoic acid [ No CAS ]

Reference： [1]Patent: CN109988065,2019,A

13
[ 88738-86-7 ]
[ 186590-01-2 ]
(E)-4-((2-cyano-5-fluorophenoxy)methyl)cinnamic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;	In a single-mouth round bottom flask,2-cyano-5-fluoro-phenol (0.68 g, 5 mmol) was dissolved in 25 ml of dry DMF.Potassium carbonate (1.38 g, 10 mmol) was added.Stir at room temperature and add (E)-4-bromomethyl benzoate (1.27 g, 5 mmol).Stirring reaction was continued for 3 h, and the reaction was complete by TLC.Quenched with water, extracted with ethyl acetate (3×30 mL).Dry over anhydrous sodium sulfate and remove the solvent under reduced pressure.Petroleum ether / dichloromethane = 1/2 elution,The white solid product was obtained in 1.36 g (yield: 87%).

Reference： [1]Patent: CN109988065,2019,A .Location in patent: Paragraph 0066-0070

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Isomers

Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blaise Reaction ? Blanc Chloromethylation ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Friedel-Crafts Reaction ? Halogenation of Phenols ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Benzene and Substituted Benzenes ? Reimer-Tiemann Reaction ? Ritter Reaction ? Thorpe-Ziegler Reaction ? Vilsmeier-Haack Reaction

Historical Records

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[ 186590-01-2 ]

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H250	Catches fire spontaneously if exposed to air
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[ CAS No. 186590-01-2 ] {[proInfo.proName]}

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Physicochemical Properties

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Medicinal Chemistry

Safety of [ 186590-01-2 ]

Application In Synthesis of [ 186590-01-2 ]

[ 186590-01-2 ] Synthesis Path-Upstream 1~1

[ 186590-01-2 ] Synthesis Path-Downstream 1~13

Technical Information

Related Functional Groups of [ 186590-01-2 ]

Fluorinated Building Blocks

Aryls

Nitriles

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[ 186590-01-2 ]