Phenyl 6-methylpyridin-3-ylcarbamate → 4-(fluoro(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)-N-(6-methylpyridin-3-yl)piperidine-1-carboxamide

Participants

Reaction Steps

To a solution of 2-(3-(fluoro(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine (110 mg, 0.312 mmol) and phenyl 6-methylpyridin-3-ylcarbamate (71.2 mg, 0.312 mmol) in DMSO (5 mL) under a N2 atmosphere was added 5 drops of triethyl amine and the reaction mixture was stirred for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water several times to remove the excess DMSO. The title compound was crystallized from hexane and diethyl ether to give the pure title compound (90 mg). 1H NMR (500 MHz, CDCl3): δ 2.5 (brs, 2H), 2.6 (brs, 2H), 2.8 (s, 3H), 3.7 (brs, 2H), 3.8 (brs, 2H), 7.0 (d, 1H, J=7.5 Hz), 7.1-7.3 (m, 3H), 7.4 (m, 2H), 7.9 (d, 1H, J=7.5 Hz), 8.4 (s, 1H), 9.0 (d, 1H, J=8.5 Hz), 9.4 (s, 1H), 9.8 (s, 1H); 13C NMR (125 MHz, CDCl3): 22.6, 25.6, 27.8, 44.2, 44.4, 53.4, 111.6, 114.1, 114.3, 121.4, 122.0, 123.8, 125.3, 129.7, 130.0, 133.8, 134.7, 136.9, 138.7, 145.4, 151.8, 153.0, 154.6, 165.4; m/z (487.4 M+ H+); HPLC: 98.9%; MP: 158-160° C.

Provenance & Evidence