(NE)-2-methyl-N-[[6-(trifluoromethyl)-3-pyridinyl]methylidene]propane-2-sulfinamide → 2-methyl-N-{(1R)-1-[6-(trifluoromethyl)-3-pyridinyl]ethyl}-2-propanesulfinamide

Temperature

-45 °C

To a solution of 2-methyl-N-{(1E)-[6-(trifluoromethyl)-3-pyridinyl]methylene}-2-propanesulfinamide (76.8 g, 276 mmol) in dichloromethane (920 mL) at −45° C. was added methylmagnesium bromide (3.0 M in tetrahydrofuran; 184 mL, 552 mmol). The mixture was stirred at −45° C. for 4 h. The reaction mixture was warmed to −20° C. Additional methylmagnesium bromide (3.0 M in tetrahydrofuran; 276 mL, 828 mmol) was added at −20° C. The reaction mixture was warmed to 0° C. and was quenched with saturated aqueous ammonium chloride (300 mL). The mixture was allowed to warm to ambient temperature. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×). The combined organic extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The concentrate was recrystallized using ethyl alcohol (500 mL). The title compound was filtered and dried under reduced pressure (41.6 g). MS 295.0 (M+1).

1. temperatureThe reaction mixture was warmed to −20° C
2. temperatureThe reaction mixture was warmed to 0° C.
3. customwas quenched with saturated aqueous ammonium chloride (300 mL)
4. temperatureto warm to ambient temperature
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with dichloromethane (3×)
7. washThe combined organic extracts were washed with saturated aqueous sodium chloride
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe concentrate was recrystallized
12. filtrationThe title compound was filtered
13. customdried under reduced pressure (41.6 g)

ORD record

ord-acf839d383324f2281fde9e5f6e7c11c

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569512B2