Cesium carbonate → 3-[(4-methoxybenzyl)oxy]-4'-phenyl-4H-1,2'-bipyridin-4-one

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave vial (Biotage) was added {3-[(4-methoxybenzyl)oxy]-4-oxo-4H-1,2′-bipyridin-4′-yl}boronic acid (300 mg, 0.85 mmol), iodobenzene (348 mg, 1.70 mmol), cesium carbonate (6 mL of a 1.0 M aq solution, 6.0 mmol), and 69.6 mg (0.085 mmol) I,Γ-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex. The vial was sealed and the reaction mixture was heated at 135° C. under microwave irradiation for 15 minutes, then cooled. The organic layer was separated, washed with 5 mL water, dried over Na2S04, filtered, and concentrated in vacuo. Purification by flash chromatography (silica gel, 0-10% MeOH in EtOAc gradient) afforded 3-[(4-methoxybenzyl)oxy]-4′-phenyl-4H-1,2′-bipyridin-4-one. LCMS (M+H)+=385.4.

Provenance & Evidence