Reaction Steps
To a solution of 2-(2-chloro-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (250 mg, 0.677 mmol) in DMSO (3 mL) was added phenyl pyridin-3-ylcarbamate (137.9 mg, 0.643 mmol) followed by triethylamine (0.24 mL, 1.69 mmol). 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 (180 mg, 54% yield). 1H NMR (500 MHz, CDCl3): δ 8.51 (s, 1H), 8.41 (s, 1H), 8.27 (s, 1H), 8.08 (d, J=7.5 Hz, 1H), 7.95 (d, J=7 Hz, 1H), 7.33 (s, 1H), 7.18 (d, J=3.5 Hz, 2H), 7.12 (d, J=8 Hz, 1H), 6.72 (s, 1H), 6.37 (s, 1H), 3.64 (m, 2H), 3.56 (m, 2H), 2.62 (m, 2H), 2.49 (m, 2H); 13C NMR (125 MHz, CDCl3): δ164.98, 154.54, 147.45, 145.35, 145.32, 143.84, 141.01, 138.68, 136.94, 136.22, 136.10, 130.79, 128.50, 127.62, 127.07, 126.69, 123.61, 123.45, 122.05, 121.78, 111.19, 45.68, 44.61, 40.91, 35.69, 29.14, 28.47; m/z (489.3, 491.1 M+ H+); HPLC: 96.8%.
