Diisopropylethylamine → N-(2-(5,6-Dichloro-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide

HRID 1777679Notes

Reaction equation

HRID 1777679 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH2:12][CH2:13][NH2:14].[F:15][C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH2:12][CH2:13][NH:14][C:24](=[O:25])[C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:18]2[CH:29]=[CH:30][CH:31]=[C:16]([F:15])[CH:17]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 133016902-(5,6-Dichloro-1H-indol-3-yl)ethanamineHCID 679746154-(3-Fluoro-benzyl)-benzoic acid

Product 1

HCID 67974674N-(2-(5,6-Dichloro-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamideYield 14.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-(5,6-Dichloro-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide was prepared according to Method A starting from 2-(5,6-dichloro-1H-indol-3-yl)ethanamine (0.149 g; 0.651 mmol), 4-(3-fluorobenzyl)benzoic acid intermediate (0.150 g, 0.651 mmol), HATU (0.248 g; 0.651 mmol) and N,N-diisopropylethylamine (0.281 mL; 1.63 mmol) in DMF (5 mL). Flash chromatography (twice) on silica gel (eluent 2 to 60% ethyl acetate in heptane and 1 to 10% ethyl acetate in dichloromethane) furnished 0.042 g (14%) of the title compound as a white solid.

Workup

  1. customN-(2-(5,6-Dichloro-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide was prepared

Sources & evidence

ORD record
ord-5a7cac77ae6f46388653c67233293680
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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