Triacetoxyperiodinane → HCID 178489407, compound

Participants

Reaction Steps

3-Fluoro-2-(4-hydroxy-cyclohexylamino)-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide (167 mg, 0.33 mmol) and 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (212 mg, 0.5 mmol; Dess-Martin periodinane) were dissolved in 5 mL dichloromethane and stirred overnight. The reaction was quenched with a saturated sodium bicarbonate solution, applied to a Varian Chemelut cartridge and eluted with ethyl acetate. Purification by flash silica gel chromatography using a gradient of ethyl acetate and hexanes afforded 3-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-2-(4-oxo-cyclohexylamino)-benzamide as a white solid (113 mg, 0.23 mmol, 68%). 1H NMR (500 MHz, DMSO-d6) δ 13.78 (s, 1H), 8.82 (s, 1H), 8.30 (s, 1H), 7.63 (m, 2H), 7.45 (m, 1H), 7.34 (s, 1H), 7.20 (d, J=10 Hz, 1H), 7.08 (t, J=8 Hz, 1H), 4.80 (d, J=9 Hz, 1H), 3.82 (s, 3H), 3.71 (m, 1H), 3.01 (bs, 3H), 2.92 (bs, 3H), 2.37 (m, 2H), 2.24 (m, 2H), 2.05 (m, 2H), 1.69 (m, 2H). MS: m/z 502.2 (M+H+).

Provenance & Evidence