Dichloromethane → 3-(benzyloxy)-5-(biphenyl-3-yl)-1-methylpyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one (38 mg, 0.129 mmol), biphenyl-3-ylboronic acid (31 mg, 0.155 mmol), PdCl2(dppf).CH2Cl2 (5.3 mg, 0.006 mmol), under nitrogen, was added THF (1 mL) followed by 1 M aqueous Na2CO3 solution (0.388 mL). The reaction mixture was heated at 150° C. (microwave irradiation) for 25 min, cooled to room temperature and partitioned between water and EtOAc. Layers were separated and the aqueous solution was extracted with CH2Cl2 (2×). Combined organic solutions were dried over Na2SO4 and concentrated. Purification by flash chromatography (24 g silica gel, 3% to 100% EtOAc in hexanes) afforded 34 mg (72%) of 3-(benzyloxy)-5-(biphenyl-3-yl)-1-methylpyridin-2(1H)-one as a white solid. LC/MS (M+H)+ 368.3.

Provenance & Evidence