Ethyl Acetate → HCID 53241674, compound

Participants

Reaction Conditions

Reaction Steps

1M BCl3 solution in DCM (0.477 mL, 0.4777 mmol) was added dropwise to a solution of 2-benzyloxymethyl-cyclopropanesulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-benzofuran-7-yl]-amide (0.150 g, 0.2388 mmol) in dry DCM (5 mL) at −75° C. and stirred for 1 hour at −75° C. The reaction mass was allowed to attain 20-35° C. and continued the stirring for 2 hours at same temperature. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mass was quenched with saturated sodium bicarbonate solution and then diluted with DCM (50 mL). The organic layer was separated, washed with water, brine solution and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (50% ethyl acetate in hexane) afforded 0.070 g of the product (55% yield). 1H NMR (DMSO-d6, 300 MHz): δ 9.38 (s, 1H), 8.19 (d, 1H), 7.77 (bs. 1H), 7.52 (dd, 1H), 7.33 (d, 1H), 7.22 (d, 1H), 6.42-6.44 (m, 1H), 4.53 (t, 1H), 3.21-3.31 (m, 1H), 3.02-3.10 (m, 1H), 1.41-1.46 (m, 1H), 1.20 (m, 1H) 0.85-0.90 (m, 1H), 0.75-0.79 (m, 1H). LCMS: 96.82%, m/z=536.9 (M−1). HPLC: 94.75%

Provenance & Evidence