Salicylaldehyde oxime → HCID 67207650, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methylpyrazole (500 mg, 6.09 mmol), salicylaldoxime (167 mg, 1.22 mmol), copper (I) oxide (44 mg, 0.30 mmol), and cesium carbonate (3.97 g, 12.2 mmol) was sparged with argon for 3 minutes. To this mixture was added acetonitrile (3 ml) and 2-bromothiophene (0.88 ml, 9.1 mmol). The reaction mixture was sparged with argon for 3 minutes and heated to 82° C. After 16 hours, the reaction mixture was diluted with ethyl acetate, washed with water and brine, then dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/hexanes gradient) to afford 3-methyl-1-(2-thienyl)-1H-pyrazole (faster eluting isomer) and 5-methyl-1-(2-thienyl)-1H-pyrazole (slower eluting isomer).

Provenance & Evidence