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

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-(bromo(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine trifluoroacetate (624 mg, 0.995 mmol) and phenyl pyridin-3-ylcarbamate (213 mg, 0.995 mmol) in DMSO (5 mL) was treated with triethyamine (0.28 mL, 201 mg, 1.99 mmol) and the mixture was heated to 60° C. After 4 h, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated and the aqueous layer was extracted again with ethyl acetate. The combine organic layers were washed with brine and dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (0-5% MeOH/CH2Cl2) to afford the title compound as a white foam (329 mg, 62% yield). MS (APCI 10V) AP+ 535.15; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (2H) 2.65 (2H) 3.46 (2H) 3.63 (2H) 6.99 (d, J=8.38 Hz, 1H) 7.05 (2H) 7.12 (dd, 1H) 7.35 (1H) 7.62 (1H) 7.87 (dd, J=8.87, 2.05 Hz, 1H) 8.13 (1H) 8.41 (1H) 8.65 (1H) 8.93 (1H) 9.20 (1H)

Provenance & Evidence