Toluene → HCID 11449329, compound

Participants

Reaction Steps

5-Cyano-7-iodo-1-phenylbenzimidazole (173 mg, 0.5 mmol), toluene (3.0 ml), tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol), pyridin-4-yl boronic acid (62 mg, 0.5 mmol), ethanol (3.0 ml) and potassium carbonate (138 mg, 1.0 mmol) were combined and the mixture was stirred at reflux overnight. The solvent was removed under reduced pressure and the crude product was purified on a 2 g silica Isolute® SPE column, eluting with dichloromethane/methanol (95:5). The eluent was concentrated under reduced pressure and the crude product was suspended in acetonitrile then treated with diethyl ether to precipitate the product. The mother liquors were removed by filtration and the residual solid was further purified on a Biotage silica gel cartridge, eluting with dichloromethane/methanol (98:2). Recrystallisation from dichloromethane/diethyl ether afforded the title compound (48 mg, 32%) m/z, 297.4 (M+H)+.

Provenance & Evidence