Tetrahydrofuran → HCID 89526146, compound

To a solution of 5-bromo-1H-indazole (2 g, 10.2 mmol) in THF (100 mL) was added sodium hydride (0.61 g, 15.2 mmol) at 0° C. for 1 hour. Dimethylsulfamoyl chloride was then added dropwise, and then the reaction mixture was allowed to reach room temperature overnight. The reaction mixture was then quenched by the addition of a saturated aqueous solution of sodium bicarbonate (100 mL), and the mixture was diluted with ethyl acetate (250 mL). The layers were separated, and the aqueous layer was extracted twice with ethyl acetate (2×250 mL). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude concentrate was purified on silica gel eluting with hexanes and ethyl acetate to afford the title compound.

1. customThe reaction mixture was then quenched by the addition of a saturated aqueous solution of sodium bicarbonate (100 mL)
2. additionthe mixture was diluted with ethyl acetate (250 mL)
3. customThe layers were separated
4. extractionthe aqueous layer was extracted twice with ethyl acetate (2×250 mL)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. concentrationThe crude concentrate
9. customwas purified on silica gel eluting with hexanes and ethyl acetate

ORD record

ord-c2493523405b4c299d1d721ac8e82477

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133157B2