Cesium carbonate → 4'-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-3'-fluoro-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one

Participants

Reaction Conditions

Reaction Steps

To a room temperature solution of 132 mg (0.292 mmol) 3′-fluoro-4′-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2′-bipyridin-4-one in 2 mL THF in a 5 mL microwave vial (Biotage) were added 253 mg (0.584 mmol) 5-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine, 1 mL 1.0 M cesium carbonate (1.0 mmol), and 23.8 mg (0.029 mmol) 1,1′-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 1 mL water, dried over Na2SO4, filtered, stirred over Quadrapure TU resin (Aldrich), concentrated in vacuo, and used without further purification.

Provenance & Evidence