N-Methoxy-N-methyl-6-(4-trifluoromethyl-phenyl)-nicotinamide → 4,4,4-Trifluoro-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-one

Participants

Reaction Conditions

Reaction Steps

N-Methoxy-N-methyl-6-(4-trifluoromethyl-phenyl)-nicotinamide (2.0 g, 6.45 mmol) is suspended in anhydrous tetrahydrofuran (25.0 mL), and cooled to 0° C. with stirring under nitrogen. 1,1,1-Trifluoro-butyl magnesium bromide (11.3 mL, 1.14M in tetrahydrofuran, 12.9 mmol) is slowly added to the reaction over 1 h. The reaction is allowed to warm slowly to room temperature and monitored by TLC. Upon complete consumption of starting material, the reaction is carefully acidified with 1N hydrochloric acid, extracted with diethyl ether, washed, dried, and concentrated. The 4,4,4-Trifluoro-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-one (1.80 g, 5.19 mmol) 80% yield, is used without further purification.

Provenance & Evidence