Water → Ethyl 4-{5-[(phenylcarbonyl)amino]pyridin-3-yl}benzenecarboxylate

Participants

Reaction Conditions

Reaction Steps

At 50° C., 5.14 g (18.2 mmol) of N-(5-bromopyridin-3-yl)benzamide, 5.40 g (27.8 mmol) of 4-ethoxycarbonylphenylboronic acid and 5.03 g (36.4 mmol) of potassium carbonate were dissolved in 30 ml of 1,2-dimethoxyethane, 9 ml of water and 65 ml of DMF. The mixture was flushed with argon, 105 mg (0.09 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 (cyclohexane/ethyl acetate 2:1→1:1). The separated solid and the appropriate fraction from the chromatography were combined. Yield: 4.6 g (60% of theory)

Provenance & Evidence