Chlorosuccinimide → HCID 89526235, compound

To a solution of methyl 3-{[1-(propan-2-ylsulfonyl)-1H-indazol-5-yl]sulfonyl}propanoate (300 mg, 0.80 mmol) in THF (4 mL) was added sodium methoxide (1.6 mL, 0.5 M, 0.80 mmol). The reaction mixture was stirred for 20 minutes, then the solvents were removed under reduced pressure and the residue was stripped down from heptanes to generate a white foam. This foam was suspended in DCM (4 mL) at 0° C. and then NCS (106 mg, 0.80 mmol) was added and the reaction mixture was stirred for 1 hour. The reaction was quenched by the addition of brine (4 mL) and the phases were separated using a phase separator. The aqueous layer was washed with DCM. The combined organic layers were concentrated under reduced pressure, and the crude was purified on silica gel eluting with hexanes and ethyl acetate to afford the title compound.

1. customthe solvents were removed under reduced pressure
2. customwas suspended in DCM (4 mL) at 0° C.
3. stirringthe reaction mixture was stirred for 1 hour
4. customThe reaction was quenched by the addition of brine (4 mL)
5. customthe phases were separated
6. washThe aqueous layer was washed with DCM
7. concentrationThe combined organic layers were concentrated under reduced pressure
8. customthe crude was purified on silica gel eluting with hexanes and ethyl acetate

ORD record

ord-e9d01360f2bd4e85b32a6bad70b82e5a

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133157B2