Acetone → 3-[(3,4-Dihydroxy-4-methylpentyl)oxy]-5-[(2-fluoro-4-iodophenyl)amino]isonicotinamide

Participants

Reaction Steps

252 mg of 3-[(2-fluoro-4-iodophenyl)amino]-5-[(4-methylpent-3-en-1-yl)oxy]isonicotinamide (0.554 mmol, 1 eq.) were dissolved in 36 ml of Acetone and 6 ml of water were added to form a suspension. Then 454 mg of N-methyl-morpholino-N-oxide 3.875, 7 eq.) and 555 μl of an osmiumtetroxide solution (2.5 weight % in tert.-butanol, 0.044 mmol, 0.08 eq.) were added and the formed suspension was stirred for 18 hours at room temperature. The reaction mixture was concentrated in vacuo and the residue was partitioned between 50 ml each of water and dichloromethane/isopropanole (4:1). The aqueouse layer was separated and reextracted twice with dichloromethane/isopropanole (4:1). The combined organic layers were washed with brine, dried over a silicone filter and concentrated to afford 272 mg (0.55 mmol, 100%) of the analytically pure target compound which required no further purification.

Provenance & Evidence