Tetrahydrofuran → HCID 89875141, compound

Temperature

-78 °C

To a solution of (R,E)-2-methyl-N-((4-methyl-5-(2,2,2-trifluoroethoxy)pyridin-2-yl)methylene)propane-2-sulfinamide (1.1 g, 3.4 mmol, Step-6) in DCM (50 mL) is added dropwise a solution of methylmagnesium bromide in THF (0.97 M, 7.0 mL, 6.8 mmol) at −78° C. After stirring at −78° C. for 1 h, the reaction is quenched with saturated aqueous ammonium chloride solution (100 mL). The aqueous layer is extracted with DCM (100 mL×2). The combined organic layer is washed with water (100 mL), and dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica-gel eluting with n-hexane/EtOAc (1:3) to give 1.09 g (94% yield) of the title compound as colorless oil.

1. customthe reaction is quenched with saturated aqueous ammonium chloride solution (100 mL)
2. extractionThe aqueous layer is extracted with DCM (100 mL×2)
3. washThe combined organic layer is washed with water (100 mL)
4. dry with materialdried over sodium sulfate
5. filtrationAfter filtration
6. concentrationthe filtrate is concentrated in vacuo
7. customThe residue is purified by column chromatography on silica-gel
8. washeluting with n-hexane/EtOAc (1:3)

ORD record

ord-df1db056715f48e480aa4704139ff5da

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187475B2