Dimethyl Sulfoxide → HCID 22244651, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dimethyl-4-phenyl-1H-pyrazole (2.50 g, 14.5 mmol), ethyl 6-chloronicotinate (5.39 g, 29.0 mmol), potassium carbonate (8.02 g, 58.1 mmol) and dimethyl sulfoxide (100 mL) was stirred at 160° C. for 16 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and toluene (2:1) and washed with water. The organic fraction was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with hexane/ethyl acetate (8:1) to afford 2.43 g (52%) of the title compound: MS (ESI) m/z 322 [M+H]+, 1H-NMR (CDCl3) δ 9.06-9.05 (1H, m), 8.39-8.36 (1H, m), 8.04-8.01 (1H, m), 7.48-7.29 (5H, m), 4.42 (2H, q, J=7.2 Hz), 2.67 (3H, s), 2.32 (3H, s), 1.43 (3H, t, J=7.2 Hz).

Provenance & Evidence