Water → 2-[3-(3-fluorophenyl)-2H-azirin-2-yl]-5-trifluoromethylpyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-fluorophenyl)-2-(5-trifluoromethyl-2-pyridinyl)ethanone oxime (3.3 g, 11.06 mmol) in CH2Cl2 (50 ml) was added Et3N (6.2 ml, 44.24 mmol). The solution was cooled to 0° C. and TFAA (1.9 ml, 13.27 mmol) was added dropwise over 30 min. After the addition was complete, the solution was stirred for an additional 5-10 min at 0° C. and then warmed to room temperature. After stirring for 1 hour at ambient temperature, the reaction was judged complete by HPLC and cooled to 0° C. Water (50 ml) was added and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×5 ml), and the combined organic extracts were dried over MgSO4. After filtration and concentration under reduced pressure, the residue was purified using column chromatography on silica gel (elution with 5-10% EtOAc in hexanes) to afford 2.5 g (81%) of the title compound as a yellow waxy solid.

Provenance & Evidence