Potassium Carbonate → 6-bromo-3-methyl-1-phenyl-1H-indazole

Participants

Reaction Conditions

Reaction Steps

Into a 500-mL 3-necked round-bottom flask, was placed a solution of (E)-1-(1-(4-bromo-2-fluorophenyl)ethylidene)-2-phenylhydrazine and (Z)-1-(1-(4-bromo-2-fluorophenyl)ethylidene)-2-phenylhydrazine (24 g, 78.18 mmol, 1.00 equiv) in N,N-dimethylformamide (200 mL), potassium carbonate (57 g, 413.04 mmol, 5.30 equiv). The resulting solution was stirred for 2 days at 100° C. in an oil bath. The resulting mixture was cooled to room temperature with a water/ice bath, then concentrated under vacuum. The residue was dissolved in water (200 mL). The resulting solution was extracted with ethyl acetate (3×150 mL) and the organic layers combined and dried over anhydrous sodium sulfate, then concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20), the resulting mixture was washed with petroleum ether (1×10 mL) to yield 6-bromo-3-methyl-1-phenyl-1H-indazole as a yellow solid. 1HNMR (400 MHz, CDCl3, ppm): δ 2.64 (3H, s), 7.30-7.87 (8H, m).

Provenance & Evidence