Reaction Steps
A degassed mixture of N-benzyl-2-chloroisonicotinamide (0.25 g, 1.01 mmol), 4-phenylpyridin-2(1H)-one (0.17 g, 0.91 mmol), potassium carbonate (0.20 g, 1.44 mmol), 8-hydroxyquiniline (0.02 g, 0.14 mmol) and copper(I) iodide (0.03 g, 0.14 mmol) in N,N-dimethylformamide (3.0 mL) was heated at 130° C. for 18 hours. The resulting solution was cooled to ambient temperature, quenched with ammonium hydroxide solution (10 mL) and extracted with ethyl acetate (2×25 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give N-benzyl-2-(2-oxo-4-phenylpyridin-1(2H)-yl)isonicotinamide as a colorless solid (0.10 g, 25%): mp 162-163° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.43 (t, J=5.1 Hz, 1H), 8.73 (d, J=5.1 Hz, 1H), 8.24, (s, 1H), 7.99 (d, J=7.3 Hz, 1H), 7.89 (d, J=5.1 Hz, 1H), 7.79-7.76 (m, 2H), 7.54-7.45 (m, 3H), 7.36-7.18 (m, 5H), 6.82 (s, 1H), 6.76 (d, J=7.3 Hz, 1H), 4.48 (d, J=5.7 Hz, 2H); 13C NMR (75 MHz, DMSO-d6) δ 164.2, 161.6, 152.7, 152.0, 150.2, 143.6, 139.4, 137.4, 136.6, 130.5, 129.6, 128.8, 127.9, 127.4, 127.3, 121.6, 119.9, 116.8, 105.6, 43.3; MS (ES+) m/z 382.6 (M+1).
