Potassium Carbonate → 1-[2-Methyl-7-(2,4,6-trimethyl-phenyl)-4,5,6,7-tetrahydro-2h-pyrazol[3,4-b]pyridine-3-yl]ethanone o-methyl-oxime

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[2-methyl-7-(2,4,6-trimethyl-phenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine-3-yl]ethanone (20 mg, 0.067 mmol), methoxylamine hydrochloride (12 mg, 0.148 mmol), and pulverized potassium carbonate (39 mg, 0.26 mmol) in 2 mL of 95% ethanol was heated at 75° C. under an atmosphere of nitrogen for 1 hr. The solvent was evaporated, the residue was treated with 50 ml of ethyl acetate, washed with brine, dried over magnesium sulfate, and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with acetone/hexane (4:96) affording 10 mg (47% yield) of 1-[2-methyl-7-(2,4,6-trimethyl-phenyl)-4,5,6,7-tetrahydro-2H-pyrazol[3,4-b]pyridine-3-yl]ethanone O-methyl-oxime (6-4) as a brown oil: ms (M+H)+=327.

Provenance & Evidence