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

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	2-(5-(trifluoromethyl)-1H-indol-3-yl)ethanamine	HCID 12030136	—
Reactant	4-(3-Fluoro-benzyl)-benzoic acid	HCID 67974615	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(3-Fluorobenzyl)-N-(2-(5-(trifluoromethyl)-1H-indol-3-yl)ethyl)benzamide	HCID 67976706	14%

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09266832B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-e66952bd1b1143498f334c5739635010
Source note	uspto-grants-2016_02