To a solution of 3-fluoro-5-iodo-2-pyridinecarbonitrile(2.31 g, 9.3 mmol) in THF (100 mL) was added 4-fluorobenzyl zinc chloride (27.9 mL, 0.5 M in THF, 14.0 mmol) followed by Pd(PPh3)4 (538 mg, 0.47 mmol). The resultant solution was heated at 75° C. (bath temperature) for 3 hours. After cooling to room temperature, water and ethyl acetate were added. The layers were separated and the organic layer was washed with brine. The aqueous layer was acidified with 1 N HCl until it cleared and extracted with ethyl acetate. The combined organics were dried over sodium sulphate. Filtration and concentration followed by purification by silica gel chromatography provided 3-fluoro-5-[(4-fluorophenyl)methyl]-2-pyridinecarbonitrile (1.6 g, 75%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 1 H), 7.28 (d, J=8.8 Hz, 1 H), 7.12 (dd, J=8.4, 5.2 Hz, 2 H), 7.03 (t, J=8.4 Hz, 2 H), 4.04 (s, 2 H). MS m/z 231 (M+1).
