Water → N-[5-(2,3-dimethylphenyl)pyridin-3-yl]benzamide

Participants

Reaction Conditions

Reaction Steps

At 50° C., 3.93 g (13.9 mmol) of N-(5-bromopyridin-3-yl)benzamide, 2.50 g (16.7 mmol) of (2,3-dimethylphenyl)boronic acid and 3.84 g (27.8 mmol) of potassium carbonate were dissolved in 50 ml of 1,2-dimethoxyethane, 17 ml of water and 100 ml of DMF. The mixture was flushed with argon, 81 mg (0.07 mmol) of tetrakis(triphenylphosphine)palladium(0) were 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→1:1). The separated solid and the appropriate fraction from the chromatography were combined. Yield: 4.2 g (96% of theory)

Provenance & Evidence