Diisopropylethylamine → N-(3-(5-Chloro-1H-indol-3-yl)propyl)-4-(3-fluorobenzyl)benzamide

HRID 1777668Notes

Reaction equation

HRID 1777668 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][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][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][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 16364293-(5-chloro-1H-indol-3-yl)propan-1-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 679746154-(3-Fluoro-benzyl)-benzoic acid

Product 1

HCID 86699440N-(3-(5-Chloro-1H-indol-3-yl)propyl)-4-(3-fluorobenzyl)benzamideYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3-(5-Chloro-1H-indol-3-yl)propyl)-4-(3-fluorobenzyl)benzamide was prepared according to method A with 3-(5-Chloro-1H-indol-3-yl)propan-1-amine (0.042 g; 0.201 mmol), 4-(3-fluorobenzyl)benzoic acid (0.049 g; 0.211 mmol), HATU (0.084 g: 0.221 mmol) and N,N-diisopropylethylamine (0.052 mL; 0.302 mmol) in DMF (3 mL). Flash chromatography on silica gel (eluent 1 to 10% ethyl acetate in dichloromethane) furnished 0.048 g (57%) of the title compound as a white solid.

Workup

  1. customN-(3-(5-Chloro-1H-indol-3-yl)propyl)-4-(3-fluorobenzyl)benzamide was prepared

Sources & evidence

ORD record
ord-f75749d79e8543a39a33b6144e7515b7
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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