Triethylamine → HCID 67973265, compound

HRID 925333Notes

Reaction equation

HRID 925333 reaction equation
[F: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][NH2:13].[C:14]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl>[F: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:20]([C:17]1[CH:18]=[CH:19][C:14]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:15][CH:16]=1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 1646825-Fluorotryptamine

Product 1

HCID 67973265HCID 67973265, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-(5-Fluoro-1H-indol-3-yl)ethyl)biphenyl-4-carboxamide was obtained following Method C starting from 2-(5-fluoro-1H-indol-3-yl)ethanamine (0.100 g, 0.561 mmol), biphenyl-4-carbonyl chloride (0.130 g; 0.589 mmol), and triethylamine (0.095 mL; 0.673 mmol) in dichloromethane (5 mL). Flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in dichloromethane) furnished 0.152 g (76%) of N-(2-(5-Fluoro-1H-indol-3-yl)ethyl)biphenyl-4-carboxamide as a white solid.

Sources & evidence

ORD record
ord-0fdb2ddbc18f4a7cb2e5d7024c90453f
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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