Sodium Carbonate → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3'-(trifluoromethyl)biphenyl-3-carboxamide

HRID 925381Notes

Reaction equation

HRID 925381 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17](I)[CH:16]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14]([C:15]1[CH:16]=[C:17]([C:28]2[CH:27]=[CH:26][C:25]([C:24]([F:35])([F:34])[F:23])=[CH:30][CH:29]=2)[CH:18]=[CH:19][CH:20]=1)=[O:22].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14]([C:15]1[CH:16]=[C:17]([C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([C:24]([F:35])([F:34])[F:23])[CH:30]=2)[CH:18]=[CH:19][CH:20]=1)=[O:22]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 17271850HCID 17271850, compound

Product 2

HCID 67973154N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3'-(trifluoromethyl)biphenyl-3-carboxamideYield 41.1%HCID 67973374N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4'-(trifluoromethyl)biphenyl-3-carboxamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4′-(trifluoromethyl)biphenyl-3-carboxamide was prepared according to method B with N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3-iodobenzamide (0.075 g; 0.176 mmol), 3-(trifluoromethyl)phenylboronic acid (0.035 g; 0.180 mmol), tetrakis(triphenylphosphine)palladium (0.010 g; 0.009 mmol), sodium carbonate (0.037 g; 0.353 mmol), in dimethoxyethane (3 mL) and water (1 mL), irradiated in a microwave oven at 130° C. for 15 minutes. Flash chromatography on silica gel (eluent 10 to 80% ethyl acetate in heptane) furnished 0.016 g (20%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-3′-(trifluoromethyl)biphenyl-3-carboxamide as a white solid.

Sources & evidence

ORD record
ord-f0e8016bf86b453e9ada037b09332c09
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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