[ CAS No. 5467-74-3 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 5467-74-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5467-74-3 ]

SDS Specification

Alternatived Products of [ 5467-74-3 ]

Product Details of [ 5467-74-3 ]

CAS No. :	5467-74-3	MDL No. :	MFCD00002104
Formula :	C₆H₆BBrO₂	Boiling Point :	-
Linear Structure Formula :	Br(C₆H₄)B(OH)₂	InChI Key :	QBLFZIBJXUQVRF-UHFFFAOYSA-N
M.W :	200.83	Pubchem ID :	79599
Synonyms :		Chemical Name :	(4-Bromophenyl)boronic acid

Calculated chemistry of [ 5467-74-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	43.97
TPSA :	40.46 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.45 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.52
Log Po/w (WLOGP) :	0.13
Log Po/w (MLOGP) :	1.05
Log Po/w (SILICOS-IT) :	-0.05
Consensus Log Po/w :	0.53

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.42
Solubility :	0.762 mg/ml ; 0.0038 mol/l
Class :	Soluble
Log S (Ali) :	-1.98
Solubility :	2.11 mg/ml ; 0.0105 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.15
Solubility :	1.44 mg/ml ; 0.00716 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.79

Safety of [ 5467-74-3 ]

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

Application In Synthesis of [ 5467-74-3 ]

* 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 [ 5467-74-3 ]
Downstream synthetic route of [ 5467-74-3 ]

[ 5467-74-3 ] Synthesis Path-Upstream 1~4

1
[ 3437-95-4 ]
[ 5467-74-3 ]
[ 40133-22-0 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2000, vol. 37, # 2, p. 281 - 286

2
[ 188290-36-0 ]
[ 5467-74-3 ]
[ 40133-22-0 ]

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 578 - 580

3
[ 188290-36-0 ]
[ 5467-74-3 ]
[ 40133-22-0 ]
[ 20608-85-9 ]

Reference： [1] Chemical Communications, 2011, vol. 47, # 42, p. 11671 - 11673

4
[ 5467-74-3 ]
[ 67-68-5 ]
[ 50907-23-8 ]

Reference： [1] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 887 - 892

[ 5467-74-3 ] Synthesis Path-Downstream 1~10

1
[ 5467-74-3 ]
[ 171408-84-7 ]
[ 1158844-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; diethylene glycol; at 80℃; for 12h;	Compound (126) (10 g, 21.08 mmol), 4-bromophenylboronic acid (4.23 g, 21.1 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (2.43 g, 21.1 mmol), aqueous 1.0 M potassium carbonate solution (105 mL) and diethyleneglycol (DME) (100 mL) were mixed, and the mixture was stirred at 80° C. under reflux for 12 hours. After cooling to ambient temperature, the organic layer was extracted with dichloromethane (200 mL), and the extract was washed with distilled water (200 mL), dried over magnesium sulfate, and distilled under reduced pressure. Purification via silica gel column chromatography (n-hexane: dichloromethane=7:1) gave Compound (127) (2.4 g, 4.4 mmol).

Reference： [1]Patent: US2011/54229,2011,A1 .Location in patent: Page/Page column 32

2
[ 5467-74-3 ]
[ 171408-84-7 ]
[ 1158844-74-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; diethylene glycol; at 80℃; for 12h;	Compound (144) (10 g, 21.1 mmol), 4-bromophenylboronic acid (4.2 g, 42.2 mmol), tetrakis(triphenylphosphine)palladium 1.0 (Pd(PPh3)4) (2.4 g, 2.1 mmol), aqueous 2.0 M potassium carbonate solution (105 mL) and diethyleneglycol (100 mL) were suspended, and the suspension was stirred at 80° C. under reflux for 12 hours. After cooling to ambient temperature, the organic layer was extracted with dichloromethane (700 mL), and the extract was washed with distilled water (400 mL), dried over magnesium sulfate, and distilled under reduced pressure. Purification via silica column chromatography (n-hexane:dichloromethane=7:1) gave Compound (146) (2.7 g, 4.4 mmol).

Reference： [1]Patent: US2011/54229,2011,A1 .Location in patent: Page/Page column 33

3
[ 5467-74-3 ]
[ 22034-13-5 ]
[ 1239277-77-0 ]

Reference： [1]Macromolecules,2010,vol. 43,p. 7101 - 7110

4
[ 5467-74-3 ]
[ 5932-27-4 ]
[ 19532-36-6 ]

Yield	Reaction Conditions	Operation in experiment
57.5%	With pyridine; oxygen; copper diacetate; In dichloromethane; at 20℃; for 16h;Molecular sieve;	To a mixture of compound XLI-1 (3.7 g, 26.6 mmol), compound XLI-2 (10.6 g, 53.4 mmol), Cu(OAc)2 and Py. in dichloromethane (400 mL) was added to powdered 4A molecular sieves. The reaction mixture was flushed with 02 and stirred at room temperature for 16 hours. The mixture was filtered through celite, the filtrated was concentrated, and the residue was purified by column chromatography (PE:EA=10:1) to give compound XLI-3 (4.5 g, yield 57.5percent).

Reference： [1]Patent: WO2013/25733,2013,A1 .Location in patent: Paragraph 0552

5
[ 1120-87-2 ]
[ 5467-74-3 ]
[ 39795-60-3 ]

Yield	Reaction Conditions	Operation in experiment
		Using similar reaction conditions as described in step i of intermediate 9, 4-bromo pyridine (2g, 8.44 mmol) was coupled with ( 4-bromophenyl) boronic acid (1 g, 9.2 mmol) in sodiumcarbonate (3.57 g, 33.7 mmol), Pd(PPh3)4 (487 mg, 0.422 mmol) and toluene/ethanol/water(50/50/20 ml) to afford 2.2 g of the crude product which was taken as such for next reaction.LCMS: 235.9 rn/z = (M+2).

Reference： [1]Patent: WO2014/6554,2014,A1 .Location in patent: Page/Page column 42

6
[ 59237-53-5 ]
[ 5467-74-3 ]
methyl 6-(4-bromophenyl)-5-nitronicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In tetrahydrofuran; water; at 75℃; for 2.5h;Inert atmosphere;	THF (46 mL) was added tripotassium phosphate (3M in H20, 4.6 mL, 13.8 mmol). After purging with N2 (vacuum/N2 x 3), the reaction was heated at 75 °C with stirring. After 2.5 h, the reaction was cooled to room temperature and concentrated. The residue was partitioned between EtOAc and H20, the organic phase was separated, washed with sat.NaC1, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, gradient of 0percent to 100percent using solvent AIB=CH2C12/EtOAc over 12 column volumes, RediSep Si02 80 g, loaded as DCM solution). A 62:26 mixture (by LCMS) of methyl 6-(4-bromophenyl)-5- nitronicotinate and methyl 6-(4?-bromo- [1,1 ?-biphenyll -4-yl)-5 -nitronicotinate (1.79 g)was obtained as a pale yellow solid, which was used as in the next step: Methyl 6-(4- bromophenyl)-5-nitronicotinate: HPLC: RT=1.31 mm (Waters Acquity UPLC BEH C18 1.7 um 2.0 x 50 mm, CH3CN/H20/0.1percentTFA, 1 mm gradient, wavelength=254nm); MS (ES): m/z= 337/339 79Br/81Br [M+lf?; methyl 6-(4?-bromo-[1,1?-biphenylj-4-yl)-5- nitronicotinate: HPLC: RT=1.53 mm (Waters Acquity UPLC BEH C18 1.7 um 2.0 x 50mm, CH3CN/H20/0. 1percentTFA, 1 mm gradient, wavelength=254nm); MS (ES): m/z=413/415 79Br/81Br [M+1j.In a 100 mL RB flask was added a mixture of methyl 6-(4-bromophenyl)-5- nitronicotinate and methyl 6-(4?-bromo- [1,1 ?-biphenyll -4-yl)-5 -nitronicotinate (1.79 g,) and 1,2-bis(diphenylphosphino)ethane (2.54 g, 6.38 mmol) in 1,2-dichlorobenzene (22 mL). The flask was placed in a pre-heated heating block at 170 °C. After 1 h, the mixture was cooled to room temperature, then concentrated in vacuo under high vacuum.The residue was dissolved in THF and a small amount of MeOH, 5i02 (20 g) was added, concentrated in vacuo then dried under vacuum overnight. The material was then purified by flash chromatography (Teledyne ISCO CombiFlash Rf, gradient of 0percent to 60percent using solvent AIBCH2C12/EtOAc over 12 column volumes, RediSep 5i02 120 g). A 3:1 mixture of methyl 7-bromo-5H-pyrido[3,2-bjindole-3-carboxylate and methyl 7-(4-bromophenyl)-5H-pyrido[3,2-bjindole-3-carboxylate (0.95 g) was obtained as a yellow solid: HPLC for methyl 7-bromo-5H-pyrido[3 ,2-bj indole-3-carboxylate: RT=0. 82 mm(Waters Acquity UPLC BEH C18 1.7 urn 2.0 x 50 mm, CH3CN/H20/0.05percentTFA, 1 mm gradient, wavelength=254nrn); MS (ES): m/z= 305/307 79Br/81Br [M+1jIn a 250 mL RB flask was added a mixture of rnethyl 7-brorno-5H-pyrido[3,2- bj indole-3 -carboxylate and rnethyl 7-(4-brornophenyl)-5H-pyrido [3 ,2-bj indole-3 - carboxylate (1.05 g, 3.44 rnrnol), 1,4-dirnethyl-5-(tributylstannyl)-1H-1,2,3-triazole (1.50 g, 3.88 rnrnol), and TEA (0.96 mL, 6.89 mmol) in DMF (49 mL), and the clear, orangesolution was purged by bubbling a nitrogen strearn through the solution for 5 mm. While purging, copper(i) iodide (107.6 rng, 0.565 mmol) and Pd(Ph3P)4 (262.5 rng, 0.227 rnrnol) were added, then the flask was fitted with a septurn, and heated in a heating block at 95°C. After 3.5 h, the reaction cooled to roorn ternperature, concentrated in vacuo, then dried under vacuurn overnight. The residue was purified by flash chrornatography(Teledyne ISCO CornbiFlash Rf, gradient of 0percent to 75percent using solvent A/B=CH2C12/acetone over 15 column volurnes, RediSep 5i02 120 g, loaded as DCM solution). Fractions containing pure product were cornbined and set aside, fractions containing irnpure product were cornbined, 5i02 (10 g) was added, and concentrated. The rnaterial was then repurified by flash chrornatography (Teledyne ISCO CornbiFlash Rf,gradient of 0percent to 70percent using solvent AIB=CH2C12/acetone over 15 column volurnes, RediSep 5i02 220 g). Once again, pure product was cornbined with product above and set aside. Irnpure product fractions were cornbined, 2 g 5i02 was added, concentrated, dried under vacuurn overnight. Repurified by flash chrornatography (Teledyne ISCO CornbiFlash Rf, gradient of 0percent to 70percent using solvent AIB=CH2C12/acetone over 20column volurnes, RediSep 5i02 40 g). Fractions containing pure product were cornbined with above product fractions and concentrated. The product, rnethyl 7-(1,4-dirnethyl-1H- 1,2,3 -triazol-5 -yl)-5H-pyrido[3 ,2-bj indole-3 -carboxylate (431.1 rng, 39percent) was obtained as ayellow solid: HPLC: RT=0.916 mm (Waters Acquity UPLC BEH C18 1.7 urn 2.0 x 50 mm, CH3CN/H20/0. 1percentTFA, 1.5 mm gradient, wavelength=254nrn); MS (ES): m/z=322 [M+ljt

Reference： [1]Patent: WO2016/183114,2016,A1 .Location in patent: Page/Page column 66; 67

7
[ 59237-53-5 ]
[ 5467-74-3 ]
methyl 7-bromo-5H-pyrido[3,2-b]indole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.95 g		THF (46 mL) was added tripotassium phosphate (3M in H20, 4.6 mL, 13.8 mmol). After purging with N2 (vacuum/N2 x 3), the reaction was heated at 75 °C with stirring. After 2.5 h, the reaction was cooled to room temperature and concentrated. The residue was partitioned between EtOAc and H20, the organic phase was separated, washed with sat.NaC1, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, gradient of 0percent to 100percent using solvent AIB=CH2C12/EtOAc over 12 column volumes, RediSep Si02 80 g, loaded as DCM solution). A 62:26 mixture (by LCMS) of methyl 6-(4-bromophenyl)-5- nitronicotinate and methyl 6-(4?-bromo- [1,1 ?-biphenyll -4-yl)-5 -nitronicotinate (1.79 g)was obtained as a pale yellow solid, which was used as in the next step: Methyl 6-(4- bromophenyl)-5-nitronicotinate: HPLC: RT=1.31 mm (Waters Acquity UPLC BEH C18 1.7 um 2.0 x 50 mm, CH3CN/H20/0.1percentTFA, 1 mm gradient, wavelength=254nm); MS (ES): m/z= 337/339 79Br/81Br [M+lf?; methyl 6-(4?-bromo-[1,1?-biphenylj-4-yl)-5- nitronicotinate: HPLC: RT=1.53 mm (Waters Acquity UPLC BEH C18 1.7 um 2.0 x 50mm, CH3CN/H20/0. 1percentTFA, 1 mm gradient, wavelength=254nm); MS (ES): m/z=413/415 79Br/81Br [M+1j.In a 100 mL RB flask was added a mixture of methyl 6-(4-bromophenyl)-5- nitronicotinate and methyl 6-(4?-bromo- [1,1 ?-biphenyll -4-yl)-5 -nitronicotinate (1.79 g,) and 1,2-bis(diphenylphosphino)ethane (2.54 g, 6.38 mmol) in 1,2-dichlorobenzene (22 mL). The flask was placed in a pre-heated heating block at 170 °C. After 1 h, the mixture was cooled to room temperature, then concentrated in vacuo under high vacuum.The residue was dissolved in THF and a small amount of MeOH, 5i02 (20 g) was added, concentrated in vacuo then dried under vacuum overnight. The material was then purified by flash chromatography (Teledyne ISCO CombiFlash Rf, gradient of 0percent to 60percent using solvent AIBCH2C12/EtOAc over 12 column volumes, RediSep 5i02 120 g). A 3:1 mixture of methyl 7-bromo-5H-pyrido[3,2-bjindole-3-carboxylate and methyl 7-(4-bromophenyl)-5H-pyrido[3,2-bjindole-3-carboxylate (0.95 g) was obtained as a yellow solid: HPLC for methyl 7-bromo-5H-pyrido[3 ,2-bj indole-3-carboxylate: RT=0. 82 mm(Waters Acquity UPLC BEH C18 1.7 urn 2.0 x 50 mm, CH3CN/H20/0.05percentTFA, 1 mm gradient, wavelength=254nrn); MS (ES): m/z= 305/307 79Br/81Br [M+1jIn a 250 mL RB flask was added a mixture of rnethyl 7-brorno-5H-pyrido[3,2- bj indole-3 -carboxylate and rnethyl 7-(4-brornophenyl)-5H-pyrido [3 ,2-bj indole-3 - carboxylate (1.05 g, 3.44 rnrnol), 1,4-dirnethyl-5-(tributylstannyl)-1H-1,2,3-triazole (1.50 g, 3.88 rnrnol), and TEA (0.96 mL, 6.89 mmol) in DMF (49 mL), and the clear, orangesolution was purged by bubbling a nitrogen strearn through the solution for 5 mm. While purging, copper(i) iodide (107.6 rng, 0.565 mmol) and Pd(Ph3P)4 (262.5 rng, 0.227 rnrnol) were added, then the flask was fitted with a septurn, and heated in a heating block at 95°C. After 3.5 h, the reaction cooled to roorn ternperature, concentrated in vacuo, then dried under vacuurn overnight. The residue was purified by flash chrornatography(Teledyne ISCO CornbiFlash Rf, gradient of 0percent to 75percent using solvent A/B=CH2C12/acetone over 15 column volurnes, RediSep 5i02 120 g, loaded as DCM solution). Fractions containing pure product were cornbined and set aside, fractions containing irnpure product were cornbined, 5i02 (10 g) was added, and concentrated. The rnaterial was then repurified by flash chrornatography (Teledyne ISCO CornbiFlash Rf,gradient of 0percent to 70percent using solvent AIB=CH2C12/acetone over 15 column volurnes, RediSep 5i02 220 g). Once again, pure product was cornbined with product above and set aside. Irnpure product fractions were cornbined, 2 g 5i02 was added, concentrated, dried under vacuurn overnight. Repurified by flash chrornatography (Teledyne ISCO CornbiFlash Rf, gradient of 0percent to 70percent using solvent AIB=CH2C12/acetone over 20column volurnes, RediSep 5i02 40 g). Fractions containing pure product were cornbined with above product fractions and concentrated. The product, rnethyl 7-(1,4-dirnethyl-1H- 1,2,3 -triazol-5 -yl)-5H-pyrido[3 ,2-bj indole-3 -carboxylate (431.1 rng, 39percent) was obtained as ayellow solid: HPLC: RT=0.916 mm (Waters Acquity UPLC BEH C18 1.7 urn 2.0 x 50 mm, CH3CN/H20/0. 1percentTFA, 1.5 mm gradient, wavelength=254nrn); MS (ES): m/z=322 [M+ljt

Reference： [1]Patent: WO2016/183114,2016,A1 .Location in patent: Page/Page column 66; 67; 68

8
[ 1047637-17-1 ]
[ 59237-53-5 ]
[ 5467-74-3 ]
methyl 7-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		THF (46 mL) was added tripotassium phosphate (3M in H20, 4.6 mL, 13.8 mmol). After purging with N2 (vacuum/N2 x 3), the reaction was heated at 75 °C with stirring. After 2.5 h, the reaction was cooled to room temperature and concentrated. The residue was partitioned between EtOAc and H20, the organic phase was separated, washed with sat.NaC1, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, gradient of 0percent to 100percent using solvent AIB=CH2C12/EtOAc over 12 column volumes, RediSep Si02 80 g, loaded as DCM solution). A 62:26 mixture (by LCMS) of methyl 6-(4-bromophenyl)-5- nitronicotinate and methyl 6-(4?-bromo- [1,1 ?-biphenyll -4-yl)-5 -nitronicotinate (1.79 g)was obtained as a pale yellow solid, which was used as in the next step: Methyl 6-(4- bromophenyl)-5-nitronicotinate: HPLC: RT=1.31 mm (Waters Acquity UPLC BEH C18 1.7 um 2.0 x 50 mm, CH3CN/H20/0.1percentTFA, 1 mm gradient, wavelength=254nm); MS (ES): m/z= 337/339 79Br/81Br [M+lf?; methyl 6-(4?-bromo-[1,1?-biphenylj-4-yl)-5- nitronicotinate: HPLC: RT=1.53 mm (Waters Acquity UPLC BEH C18 1.7 um 2.0 x 50mm, CH3CN/H20/0. 1percentTFA, 1 mm gradient, wavelength=254nm); MS (ES): m/z=413/415 79Br/81Br [M+1j.In a 100 mL RB flask was added a mixture of methyl 6-(4-bromophenyl)-5- nitronicotinate and methyl 6-(4?-bromo- [1,1 ?-biphenyll -4-yl)-5 -nitronicotinate (1.79 g,) and 1,2-bis(diphenylphosphino)ethane (2.54 g, 6.38 mmol) in 1,2-dichlorobenzene (22 mL). The flask was placed in a pre-heated heating block at 170 °C. After 1 h, the mixture was cooled to room temperature, then concentrated in vacuo under high vacuum.The residue was dissolved in THF and a small amount of MeOH, 5i02 (20 g) was added, concentrated in vacuo then dried under vacuum overnight. The material was then purified by flash chromatography (Teledyne ISCO CombiFlash Rf, gradient of 0percent to 60percent using solvent AIBCH2C12/EtOAc over 12 column volumes, RediSep 5i02 120 g). A 3:1 mixture of methyl 7-bromo-5H-pyrido[3,2-bjindole-3-carboxylate and methyl 7-(4-bromophenyl)-5H-pyrido[3,2-bjindole-3-carboxylate (0.95 g) was obtained as a yellow solid: HPLC for methyl 7-bromo-5H-pyrido[3 ,2-bj indole-3-carboxylate: RT=0. 82 mm(Waters Acquity UPLC BEH C18 1.7 urn 2.0 x 50 mm, CH3CN/H20/0.05percentTFA, 1 mm gradient, wavelength=254nrn); MS (ES): m/z= 305/307 79Br/81Br [M+1jIn a 250 mL RB flask was added a mixture of rnethyl 7-brorno-5H-pyrido[3,2- bj indole-3 -carboxylate and rnethyl 7-(4-brornophenyl)-5H-pyrido [3 ,2-bj indole-3 - carboxylate (1.05 g, 3.44 rnrnol), 1,4-dirnethyl-5-(tributylstannyl)-1H-1,2,3-triazole (1.50 g, 3.88 rnrnol), and TEA (0.96 mL, 6.89 mmol) in DMF (49 mL), and the clear, orangesolution was purged by bubbling a nitrogen strearn through the solution for 5 mm. While purging, copper(i) iodide (107.6 rng, 0.565 mmol) and Pd(Ph3P)4 (262.5 rng, 0.227 rnrnol) were added, then the flask was fitted with a septurn, and heated in a heating block at 95°C. After 3.5 h, the reaction cooled to roorn ternperature, concentrated in vacuo, then dried under vacuurn overnight. The residue was purified by flash chrornatography(Teledyne ISCO CornbiFlash Rf, gradient of 0percent to 75percent using solvent A/B=CH2C12/acetone over 15 column volurnes, RediSep 5i02 120 g, loaded as DCM solution). Fractions containing pure product were cornbined and set aside, fractions containing irnpure product were cornbined, 5i02 (10 g) was added, and concentrated. The rnaterial was then repurified by flash chrornatography (Teledyne ISCO CornbiFlash Rf,gradient of 0percent to 70percent using solvent AIB=CH2C12/acetone over 15 column volurnes, RediSep 5i02 220 g). Once again, pure product was cornbined with product above and set aside. Irnpure product fractions were cornbined, 2 g 5i02 was added, concentrated, dried under vacuurn overnight. Repurified by flash chrornatography (Teledyne ISCO CornbiFlash Rf, gradient of 0percent to 70percent using solvent AIB=CH2C12/acetone over 20column volurnes, RediSep 5i02 40 g). Fractions containing pure product were cornbined with above product fractions and concentrated. The product, rnethyl 7-(1,4-dirnethyl-1H- 1,2,3 -triazol-5 -yl)-5H-pyrido[3 ,2-bj indole-3 -carboxylate (431.1 rng, 39percent) was obtained as ayellow solid: HPLC: RT=0.916 mm (Waters Acquity UPLC BEH C18 1.7 urn 2.0 x 50 mm, CH3CN/H20/0. 1percentTFA, 1.5 mm gradient, wavelength=254nrn); MS (ES): m/z=322 [M+ljt

Reference： [1]Patent: WO2016/183114,2016,A1 .Location in patent: Page/Page column 66; 67; 68

9
[ 5467-74-3 ]
[ 57103-20-5 ]
C₃₀H₁₉Br₂N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78.1%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; toluene; at 60 - 65℃; for 24h;Inert atmosphere;	Under nitrogen protection,The resulting intermediate A-1 (20.1 g, 0.05 mol) and p-bromophenylboronic acid (20.1 g,0.1 mol) was put into a solution of 200 g of toluene and 50 g of THF, and then an aqueous solution of potassium carbonate (300 mL, 1 mol / L)Finally, the catalyst Pd (PPh3) 4 (0.58 g, 0.5 mmol) was charged.The reaction system was heated to 60 to 65 ° C and stirred for 24 hours.After completion of the reaction, 100 mL of water was added to the reaction system,Quenching reaction,Filtration is not no,The resulting filtrate was washed with deionized water,Concentrated under reduced pressure,The crude material was crystallized from ethyl acetate or petroleum ether,To give a white solid,The intermediate B-1 was obtained78.1percent.
75%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; toluene; at 60 - 65℃; for 24h;Inert atmosphere;	Under nitrogen protection,The intermediate a (20.05 g, 0.05 mol) obtained in the previous step and p-bromophenylboronic acid (20.08 g, 0.1 mol) were charged into a mixed solvent of 200 g of toluene and 50 g of THF,Then, an aqueous solution of potassium carbonate (300 mL, 1 mol / L)Finally, catalyst Pd (PPh3) 4 (0.58 g, 0.5 mmol) was charged.The reaction system was warmed to 60-65 ° C and stirred for 24 hours.After the reaction was completed, 100 mL of water was added to the reaction system to quench the reaction and the insoluble materials were filtered off to obtain a filtrate. After washing with deionized water and concentrated under reduced pressure, the crude product was crystallized from ethyl acetate or petroleum ether to give a white solid For the intermediate b, yield 75percent.

Reference： [1]Patent: CN105906612,2016,A .Location in patent: Paragraph 0068; 0069
[2]Patent: CN105175405,2017,B .Location in patent: Paragraph 0042-0044

10
[ 52133-67-2 ]
[ 5467-74-3 ]
ethyl 2-(4-bromophenyl)-1H-pyrrole-3-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2214 - 2217

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? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? Hydrogenolysis of Benzyl Ether ? Preparation of Alkylbenzene ? Reactions of Benzene and Substituted Benzenes ? Vilsmeier-Haack Reaction

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