Dimethylformamide → HCID 25144318, compound

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	2-Pyridinemethanamine	HCID 19509	—
Reactant	3-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole	HCID 23159812	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	HCID 25144318	HCID 25144318	34%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (1.02 g, 2.24 mmol), 2-picolylamine (369 mg, 3.41 mmol), Pd(dppf)Cl2 (92 mg, 0.13 mmol) triethylamine (5.2 mL, 3.8 g. 37 mmol) and DMF (50 mL) was flushed with carbon monoxide and stirred under an atmosphere of CO at 100° C. for 26 h. The solvent was removed in vacuum and the residue was taken up in EtOAc, filtered and evaporated. The residue was chromatographed on SiO2 to give the title compound (391 mg, 34%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08853410B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-ba93eb5412dd4ea4ba999b5c04514fc0
Source note	uspto-grants-2014_10