Reaction Steps
To a solution of 2-(2-methyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (440 mg, 0.001 mol) in DMSO (5 mL) was added phenyl pyridin-3-ylcarbamate (278 mg, 0.001 mol) followed by triethylamine (0.4 mL, 0.003 mol). The resulting mixture was stirred at RT for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (30% acetone-70% hexane) to give the pure title compound (0.310 g, 50%). 1H NMR (500 MHz, CDCl3): δ 8.45-8.42 (m, 2H), 8.26 (d, J=4.5 Hz, 1H), 8.01 (d, J=7 Hz, 1H), 7.91 (d, J=9 Hz, 1H), 7.25-7.22 (m, 1H), 7.05-6.99 (m, 2H), 6.91 (s, 1H), 6.63 (s, 1H), 6.37 (s, 1H), 3.62 (t, J=5.5 Hz, 2H), 3.53 (t, J=11.5 Hz, 2H), 2.63-2.58 (m, 2H), 2.46 (t, J=5.5 Hz, 2H), 2.14 (s, 3H); 13C NMR (125 MHz, CDCl3): δ 165.61, 154.45, 151.24, 145.65, 144.06, 141.14, 137.34, 136.77, 136.49, 136.05, 131.34, 128.95, 127.36, 126.42, 124.45, 123.59, 122.18, 110.76, 45.71, 44.60, 35.69, 29.14, 16.09; m/z (469.5, M+ H+); HPLC: 98.8%.
