Ethyl Acetate → HCID 178440517, compound

Participants

Reaction Conditions

Reaction Steps

TEA (02611 g, 2.581 mmol) was added to a solution of 4,5-difluoro-3-(2-fluoro-4-iodophenyl)-1H-benzofuro[6,7-d]imidazol-2(3H)-one (I-32a: 0.37 g, 0.8604 mmol) in dry DCM (20 mL) at 0° C. This was followed by the addition of 1-allyl-cyclopropanesulfonyl chloride (0.229 g, 1.89 mmol) and catalytic amount of DMAP (10 mg). The reaction mass was stirred for 12 hours at 20-40° C. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mass was diluted with DCM (50 mL) and partitioned between water and DCM. The organic layer was washed with water, brine solution and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (20% ethyl acetate in hexane) afforded 0.228 g of the product (46% yield). 1H NMR (CDCl3, 300 MHz): δ 7.71 (dd, 3H), 7.30 (t, 1H), 7.00 (s, 1H), 5.56-5.57 (m, 1H), 4.90 (t, 2H), 2.70-2.80 (q, 2H), 1.90-2.05 (m, 2H), 1.10-1.19 (m, 2H). LCMS: 98.85%, m/z=574.4 (M+1). HPLC: 97.1%

Provenance & Evidence