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

HRID 2113800Notes

Reaction equation

[CH3:1][N:2]1[C:10]([C:11](=O)[CH3:12])=[C:9]2[C:4]([N:5]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])[CH2:6][CH2:7][CH2:8]2)=[N:3]1.Cl.[O:24]([NH2:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:25][O:24][N:26]=[C:11]([C:10]1[N:2]([CH3:1])[N:3]=[C:4]2[C:9]=1[CH2:8][CH2:7][CH2:6][N:5]2[C:14]1[C:15]([CH3:22])=[CH:16][C:17]([CH3:21])=[CH:18][C:19]=1[CH3:20])[CH3:12]

Participants

Conditions

Temperature: 75 °C

Procedure

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.

Workup

customThe solvent was evaporated
additionthe residue was treated with 50 ml of ethyl acetate
washwashed with brine
dry with materialdried over magnesium sulfate
customevaporated to dryness
customThe residue was purified by flash chromatography on silica gel eluting with acetone/hexane (4:96)

Sources & evidence

ORD record: ord-a5de7b69e678490f9c81aadf1f56b4a4
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432283B2

Reaction notes

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