Isopropanol → 3-Bromo-2-methyl-7-(2,4,6-trimethylphenyl)-2,4,5,7-tetrahydro-pyrazolo[3,4-b]pyridin-6-one

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Reaction Steps

Ruthenium(IV) oxide hydrate (22 mg) was dissolved in 35 mL water and sodium periodate (684 mg) was added. This mixture was rapidly stirred while 3-bromo-2-methyl-7-(2,4,6-trimethyl-phenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine (1-3; 505 mg) in 25 mL carbon tetrachloride was added dropwise. After the mixture had stirred at room temperature over night, isopropanol was added and the mixture was stirred for an additional hour. The mixture was then filtered through diatomaceous earth and extracted with dichloromethane. The organic extracts were dried with magnesium sulfate and concentrated. The residue was chromatographed on silica gel to afford 54.4 mg of 3-bromo-2-methyl-7-(2,4,6-trimethylphenyl)-2,4,5,7-tetrahydro-pyrazolo[3,4-b]pyridin-6-one (9-4).

Provenance & Evidence