Diisopropylethylamine → N-(2-(5-Chloro-2-methyl-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)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-chloro-2-methyl-1H-indol-3-yl)ethanamine hydrochloride	HCID 16495330	—
Reactant	4-(3-Fluoro-benzyl)-benzoic acid	HCID 67974615	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(2-(5-Chloro-2-methyl-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide	HCID 67974677	34%

Reaction Steps

N-(2-(5-Chloro-2-methyl-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide was prepared according to method A with 4-(3-fluorobenzyl)benzoic acid (0.080 g, 0.347 mmol), 2-(5-chloro-2-methyl-1H-indol-3-yl)ethanamine hydrochloride (0.094 g; 0.382 mmol), HATU (0.132 g; 0.347 mmol) and N,N-diisopropylethylamine (0.150 mL; 0.869 mmol) in DMF (5 mL). Flash chromatography on silica gel (eluent 20 to 100% ethyl acetate in heptane) furnished 0.049 g (34%) of the title compound as a pale yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09266832B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-a7b93dc28d24483583c177bb760b2194
Source note	uspto-grants-2016_02