Sodium periodate → HCID 86697085, compound

Participants

Reaction Steps

Osmium (VIII) oxide (2.5% wt in tert-butanol, 0.1 mL) was added to a solution of 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-vinylbenzonitrile (42 mg, 0.1 mmol) in acetone (2.0 mL) and water (0.5 mL). Sodium periodate (47 mg, 0.22 mmol) was then added and the reaction mixture was stirred at room temperature overnight. The resultant mixture was partitioned between ethyl acetate and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (70-80% ethyl acetate in cyclohexane) to afford the title compound as a yellow glass (24 mg, 60% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.89 (s, 1H), 10.12 (s, 1H), 9.55 (d, J=2.5 Hz, 1H), 8.72-8.62 (m, 3H), 8.37 (s, 1H), 8.03 (d, J=3.4 Hz, 1H), 2.45 (s, 3H).

Provenance & Evidence