Reaction Steps
A degassed mixture of N-benzyl-2-chloroisonicotinamide (0.05 g, 0.20 mmol), 4-phenylpiperidin-2-one (0.04 g, 0.22 mmol), cesium carbonate (0.20 g, 0.61 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.005 g, 0.008 mmol), tris(dibenzylideneacetone)dipalladium (0.004 g, 0.004 mmol) in N,N-dimethylformamide (3.0 mL) was heated at 90° C. for 18 hours and cooled to ambient temperature. The resulting solution was diluted with ethyl acetate (30 mL), washed with water (20 mL) and brine (20 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give 2-oxo-4-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4′-carboxylic acid benzylamide as a colorless solid (0.06 g, 77%): mp 55-60° C.; 1H NMR (300 MHz, CDCl3) δ 8.46 (d, J=5.1 Hz, 1H), 8.09 (s, 1H), 7.50 (d, J=5.1 Hz, 1H), 7.40-7.16 (m, 11H), 4.59-4.46 (m, 2H), 4.09-3.84 (m, 2H), 3.24-3.09 (m, 1H), 2.79 (dd, J=17.5, 5.3 Hz, 1H), 2.61 (dd, J=17.5, 11.2 Hz, 1H), 2.26-2.22 (m, 1H), 2.13-1.95 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 170.6, 165.1, 154.8, 148.7, 143.2, 142.9, 137.8, 128.9, 128.7, 128.1, 127.6, 127.0, 126.5, 119.0, 117.8, 47.4, 44.1, 40.8, 38.6, 30.3; MS (ES+) m/z 386.5 (M+1).
