Potassium Carbonate → 6-[(5-Chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)methyl]-5-methyl-2-pyridinecarbonitrile

Participants

Reaction Steps

To a solution of 6-(chloromethyl)-5-methyl-2-pyridinecarbonitrile (132.5 mg) in dry toluene (4 ml) and ethanol (4 ml) was added (5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)boronic acid (250 mg), potassium carbonate (330 mg) and tetrakis(triphenylphosphine)palladium(0) (92 mg) and the mixture stirred under reflux for 2 hours. Solvent was removed in vacuo and water (20 ml) and ether (20 ml) added. Insoluble solid was filtered over Celite and washed with ether. The aqueous layer was further extracted with ether (15 ml) and the combined extracts washed with brine (10 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by mass-directed autopreparation to afford the title compound (129 mg, 40%) as a pale buff solid.

Provenance & Evidence