Water → N-{5-[4-(Trifluoromethoxy)phenyl]pyridin-3-yl}benzenecarboxamide

Participants

Reaction Conditions

Reaction Steps

At 50° C., 11.8 g (41.4 mmol) of N-(5-bromopyridin-3-yl)benzamide, 12.8 g (62.1 mmol) of [4-(trifluoromethoxy)phenyl]boronic acid and 11.4 g (82.7 mmol) of potassium carbonate were dissolved in 70 ml of 1,2-dimethoxyethane, 21 ml of water and 156 ml of DMF. The mixture was flushed with argon, 0.24 g (0.2 mmol) of tetrakis(triphenylphosphine)palladium(0) was added and the mixture was stirred at 85° C. for 12 h. The reaction mixture was concentrated slightly on a rotary evaporator, diluted with water and extracted with dichloromethane. The organic phase was concentrated under reduced pressure and the residue was triturated with methyl tert-butyl ether. The solid was filtered off and the filtrate was purified by column chromatography on silica gel (cyclohexane/ethyl acetate 2:1=>1:5). The separated solid and the appropriate fraction from the chromatography were combined. Yield: 6.7 g (45% of theory)

Provenance & Evidence