Triethylamine → N-(2-(5-Chloro-1H-indol-3-yl)ethyl)biphenyl-3-carboxamide

HRID 925337Notes

Reaction equation

HRID 925337 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH2:14].[C:15]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][CH:18]=[C:17]([C:21](Cl)=[O:22])[CH:16]=1.C(N(CC)CC)C>ClCCl>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH:14][C:21]([C:17]1[CH:16]=[C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756666Biphenyl-3-carbonyl chlorideHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochloride

Product 1

HCID 67973107N-(2-(5-Chloro-1H-indol-3-yl)ethyl)biphenyl-3-carboxamideYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-(5-Chloro-1H-indol-3-yl)ethyl)biphenyl-3-carboxamide was obtained following Method C starting from 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.100 g, 0.424 mmol), biphenyl-3-carbonyl chloride (0.0965 g; 0.445 mmol), and triethylamine (0.145 mL; 1.06 mmol) in dichloromethane (5 mL). Flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane) furnished 0.0565 g (36%) of N-(2-(5-Chloro-1H-indol-3-yl)ethyl)biphenyl-3-carboxamide as a white solid.

Sources & evidence

ORD record
ord-8879f0c2460c4fed82da07b933ccaa1a
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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