Methanol → HCID 53241675, compound

Participants

Reaction Conditions

Reaction Steps

N-methyl morpholine oxide (0.035 g, 0.3041 mmol) was added to a solution of 1-allyl-cyclopropane sulfonic acid [4,5-difluoro-6-(2-fluoro-4-iodo-phenylamino)-benzofuran-7-yl]-amide (0.167 g, 0.3041 mmol) in THF (5 mL). This was followed by the addition of osmium tetroxide (0.0077 g, 0.03041 mmol) in water (1 mL). The reaction mass was stirred for 16 hours at 30-40° C. The reaction was monitored by TLC (10% methanol in chloroform). The reaction mass was partitioned between ethyl acetate (50 mL) and water. The organic layer was washed with water (3×50 mL), brine solution and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (5% methanol in chloroform) afforded 0.090 g of the product (50% yield). 1H NMR (CDCl3, 300 MHz): δ 7.69 (d, 2H), 7.40 (dd, 1H), 7.25 (s, 1H), 6.99 (d, 1H), 6.98 (bs, 1H), 6.38-6.40 (m, 1H), 4.25 (bs, 1H), 3.62 (dd, 2H), 3.32 (d, 1H), 2.55 (q, 1H), 2.22 (bs, 1H), 1.75 (t, 2H), 138-1.40 (m, 2H). LCMS: 99.49%, m/z=582.9 (M+1). HPLC: 95.29%

Provenance & Evidence