Ethanol → 3-{[6-(2,4-Difluorophenyl)pyridin-2-yl]methyl}-4-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[(6-bromopyridin-2-yl)methyl]-4-fluorobenzonitrile (from Step B above, 8.34 g, 28.6 mmol) in toluene (300 mL) was added (2,4-difluorophenyl)boronic acid (8.15 g, 34.4 mmol), tetrakis(triphenylphosphine)palladium (1.65 g, 1.40 mmol), ethanol (30 mL), and 2M Na2CO3 (30 mL). The resulting mixture was heated to 95° C. for 2 hours. The reaction was cooled to room temperature and filtered through celite and concentrated in vacuo. The crude residue was dissolved in EtOAc, washed with H2O, brine (2×), dried over MgSO4, and concentrated. The crude material was purified via silica gel chromatography (hexanes/ethyl acetate) to give the title compound as a white solid (7.03 g).

Provenance & Evidence