Reaction Steps
2-(3-Fluoro-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (469 mg, 1.33 mmol) and phenyl pyridin-3-ylcarbamate (273 mg, 1.33 mmol) were dissolved in DMSO (4 mL) and triethylamine (0.53 mL, 3.83 mmol) was added. The reaction was stirred overnight. The reaction mixture was diluted with water and extracted with ethyl acetate three times. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by silica gel column chromatography (35% acetone in hexane) to give the title compound (500 mg, 80%). 1H NMR (500 MHz, CDCl3): δ 8.51 (s, 1H), 8.45 (s, 1H), 8.27 (d, J=4.5 Hz, 1H), 8.08 (d, J=8 Hz, 1H), 7.95 (d, J=9 Hz, 1H), 7.06 (d, J=8.5 Hz, 1H), 6.82 (m, 3H), 6.71 (s, 1H), 6.37 (s, 1H), 3.64 (t, J=5.5 Hz, 2H), 3.56 (t, J=5.5 Hz, 2H), 2.63 (m, 2H), 2.49 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 165.15, 163.96, 161.99, 154.67, 153.88, 153.79, 145.40, 143.56, 141.00, 140.15, 140.07, 139.38, 136.97, 136.44, 127.78, 124.64, 123.69, 122.49, 122.23, 121.97, 117.60, 112.87, 112.70, 111.71, 107.56, 107.37, 45.59, 44.54, 35.70, 29.18; m/z (473.4 M+ H+); HPLC: 96.6%.
