Dimethylformamide → n-((5-Chloro-1h-indol-3-yl)methyl)-5-(3-fluorobenzyl)isoxazole-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Ethyl Acetate	HCID 8857	—
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	(5-Chloro-1H-indol-3-yl)methanamine	HCID 21281458	—
Solvent	Dichloromethane	HCID 6344	—
Product	n-((5-Chloro-1h-indol-3-yl)methyl)-5-(3-fluorobenzyl)isoxazole-3-carboxamide	HCID 66831683	22%

Reaction Steps

This compound was prepared following Method A starting from (5-chloro-1H-indol-3-yl)methanamine (0.060 g; 0.332 mmol), the intermediate 11 (0.081 g; 0.365 mmol), HATU (0.139 g; 0.365 mmol) and N,N-diisopropylethylamine (0.075 mL; 0.432 mmol) in DMF (5 mL). Flash chromatography on silica gel eluting with 2 to 10% of ethyl acetate in dichloromethane afforded 0.028 g (22%) of N-((5-chloro-1H-indol-3-yl)methyl)-5-(3-fluorobenzyl)isoxazole-3-carboxamide as a solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434722B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-a3987e0d68e241ce850cd402def5523c
Source note	uspto-grants-2016_09