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

Temperature

0 °C

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.

1. additionAfter the addition
2. temperaturewarmed to room temperature
3. stirringAfter stirring for 1 hour at ambient temperature
4. temperaturecooled to 0° C
5. customthe layers were separated
6. extractionThe aqueous layer was extracted with CH2Cl2 (2×5 ml)
7. dry with materialthe combined organic extracts were dried over MgSO4
8. filtrationAfter filtration and concentration under reduced pressure
9. customthe residue was purified

ORD record

ord-ed098643293e4291b832e093704c5846

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06756498B2