Diisopropylethylamine → 4-(3-Fluorobenzyl)-N-(2-(5-(trifluoromethyl)-1H-indol-3-yl)ethyl)benzamide

HRID 1777677Notes

Reaction equation

HRID 1777677 reaction equation
[F:1][C:2]([F:16])([F:15])[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].[F:17][C:18]1[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=1)[CH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=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>[F:17][C:18]1[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=1)[CH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:14][CH2:13][CH2:12][C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([C:2]([F:15])([F:1])[F:16])[CH:4]=3)[NH:8][CH:7]=2)=[O:27])=[CH:24][CH:23]=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 120301362-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamineHCID 679746154-(3-Fluoro-benzyl)-benzoic acid

Product 1

HCID 679767064-(3-Fluorobenzyl)-N-(2-(5-(trifluoromethyl)-1H-indol-3-yl)ethyl)benzamideYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-Fluorobenzyl)-N-(2-(5-(trifluoromethyl)-1H-indol-3-yl)ethyl)benzamide was prepared according to Method A starting from 2-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamine (0.080 g; 0.347 mmol), 4-(3-fluorobenzyl)benzoic acid (0.080 g, 0.347 mmol), HATU (0.132 g; 0.347 mmol) and N,N-diisopropylethylamine (0.149 mL; 0.869 mmol) in DMF (3 mL). The crude material was purified by preparative HPLC (method 2) to afford 0.021 g (14%) of the title compound as a white solid.

Workup

  1. custom4-(3-Fluorobenzyl)-N-(2-(5-(trifluoromethyl)-1H-indol-3-yl)ethyl)benzamide was prepared
  2. customThe crude material was purified by preparative HPLC (method 2)

Sources & evidence

ORD record
ord-e66952bd1b1143498f334c5739635010
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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