HCID 89479433, compound → HCID 86730199, compound

Temperature

0 °C

To a solution of (R,E)-N-(4-(difluoromethyl)-2-fluorobenzylidene)-2-methylpropane-2-sulfinamide (266 mg, 0.959 mmol) in DCM (9.6 mL) was added methylmagnesium bromide (3M in diethylether; 1.20 mL) at 0° C. The reaction mixture was allowed to stir for 30 min at 0° C., gradually allowed to warm to room temperature and stirred for 1 hour at room temperature. The mixture was cooled to 0° C., and carefully quenched with saturated aqueous NH4Cl solution (3 mL). The separated aqueous phase was extracted with DCM. The combined organic layers were washed with brine, dried over sodium sulfate, filtered off and concentrated under reduced pressure. The crude material was purified by column chromatography [SiO2, 40 g, heptane/ethyl acetate], providing (R)—N—((S)-1-(4-(difluoromethyl)-2-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (160.5 mg) as a white solid. LCMS m/z 294.5 (M+H)+, Rt 0.85 min.

1. temperatureto warm to room temperature
2. stirringstirred for 1 hour at room temperature
3. temperatureThe mixture was cooled to 0° C.
4. customcarefully quenched with saturated aqueous NH4Cl solution (3 mL)
5. extractionThe separated aqueous phase was extracted with DCM
6. washThe combined organic layers were washed with brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered off
9. concentrationconcentrated under reduced pressure
10. customThe crude material was purified by column chromatography [SiO2, 40 g, heptane/ethyl acetate]

ORD record

ord-4886be8b8705433098ce6b15615f59a4

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957068B2