Ethanol → HCID 90092917, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromo-1-methyl-3-phenyl-1H-pyrazole-5-carbaldehyde (1c) (150 mg, 0.57 mmol), sodium carbonate (240 mg, 2.26 mmol), and 4,4-(dimethylcyclohexene-1-yl)boronic acid pinacol ester (174 mg, 0.74 mmol) in a mixture of toluene (0.8 mL), ethanol (0.3 mL) and water (0.3 mL) was bubbled with nitrogen for 5 minutes. Palladium tetrakis(triphenylphosphine) (32.7 mg, 0.028 mmol) was added and the reaction mixture was heated at 95° C. overnight. The solution was concentrated in vacuo. Water (3 mL) was added to the residue. The aqueous layer was extracted with ethyl acetate (2×5 mL) and the organic layer was dried over sodium sulfate and concentrated in vacuo. The crude was purified by preparative TLC (cyclohexane/ethyl acetate 80/20) to provide 4-(4,4-dimethylcyclohex-1-en-1-yl)-1-methyl-3-phenyl-1H-pyrazole-5-carbaldehyde (1d) (135 mg, 0.46 mmol, 81%).

Provenance & Evidence