N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide → Cyclopropyl(6-(trifluoromethyl)pyridin-3-yl)methanone

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-methoxy-N-methyl-6-(trifluoromethyl)nicotinamide (1.00 g, 4.27 mmol) in tetrahydrofuran (30 mL) at 0° C. was added 0.5 M of cyclopropylmagnesium bromide in tetrahydrofuran (20 mL, 0.01 mol) dropwise over 15 minutes. The mixture was stirred at 0° C. for 30 minutes then at room temperature overnight. The reaction was quenched with 1N HCl. Solvent was pumped off and the water layer was extracted with ethyl acetate. Organics were combined and dried with MgSO4, filtered and concentrated to obtain a crude brown oil. The crude product was purified by silica gel column (0-60% ethyl acetate/hexane) to obtain a pale yellow solid.

Provenance & Evidence