Diethyl Ether → 4-(phenyl(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)-N-(pyridin-3-yl)piperidine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of phenyl pyridin-3-ylcarbamate (27.1 mg, 0.127 mmol) in DMSO (3 mL) was added 2-(3-(phenyl(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine trifluoroacetate (52 mg, 0.13 mmol), followed by triethylamine (0.018 mL, 0.127 mmol). The reaction was stirred at 60° C. for 3 h and then cooled to RT. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with water and saturated aqueous NH4Cl, dried and concentrated. Purification by silica gel column chromatography (0-5% MeOH/CH2Cl) gave an oil. Diethyether was added followed by CH2Cl2 and the title compound crashed out as a solid (9.2 mg, 13% yield). MS (APCI 10V) AP+ 531.23; 1H NMR (400 MHz, CDCl3) δ ppm 2.43 (t, 2H) 2.50 (t, 2H) 3.51-3.58 (m, 4H) 6.75 (s, 1H) 6.90-6.92 (m, 1H) 6.94-7.04 (m, 2H) 7.12 (dd, 2H) 7.17-7.23 (m, 3H) 7.26-7.37 (m, 3H) 7.86 (dd, 1H) 7.97 (dd, 1H) 8.23 (br. s., 1H) 8.42 (s, 2H).

Provenance & Evidence