Water → HCID 19697339, compound

Participants

Reaction Steps

To a solution of 995 mg (2.32 mmol) of 5-bromo-2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4,5,6,7-tetrahydro-6-hydroxy-1H-isoindole-1,3(2H)-dione in 15 mL of dichloromethane was added 430 μL of DAST at 0° C. The mixture was stirred at the same temperature for 1 h. The reaction mixture was then poured into 50 mL of cold water. The aqueous layer was extracted with three 50 mL portions of ethyl acetate. The organic layers were dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel eluting with a 1:4 v:v mixture of ethyl acetate and n-hexane to give 626 mg of the title product of Example 4, a compound of the invention, as a whim solid melting at 135°-136.5° C.

Provenance & Evidence