Methyl iodide → HCID 57899237, compound

Participants

Reaction Steps

A mixture of (5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-acetic acid methyl ester and (3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-acetic acid methyl ester (678 mg, 2.75 mmol), K2CO3 (pulverized, 1.45 g, 10.5 mmol), and methyl iodide (0.7 mL, 11 mmol) in acetonitrile 10 mL) was refluxed for 1 h and cooled to room temperature. The reaction mixture was diluted with water (40 mL) and extracted with ethyl acetate (3×100 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified via silica gel column chromatography to give (5-methoxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-acetic acid methyl ester (86.5 mg, 12%), (3,4-dimethyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-acetic acid methyl ester (161 mg, 22%) and (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-acetic acid methyl ester (417 mg, 58%). LCMS 261.2 (M+1).

Provenance & Evidence