Trifluoroacetic anhydride → 2-Methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-benzonitrile

Participants

Reaction Conditions

Reaction Steps

(R)-2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-benzamide (230 mg, 0.47 mmol) was dissolved in pyridine (5 mL) and cooled to 0° C. Trifluoroacetic anhydride (0.67 mL, 4.72 mmol) was added dropwise. Stirred for 1 h at 0° C. after addition. The reaction was diluted with diethyl ether (100 mL) and washed with 1 N HCl (2×100 mL) and saturated NaHCO3 (100 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was flash chromatographed with 33% ethyl acetate/hexanes to yield 262 mg (97%) of the desired 2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-benzonitrile as a clear oil.

Provenance & Evidence