Sodium t-butoxide → 2-(4-methoxyphenyl)-2H-indazole

Participants

Reaction Conditions

Reaction Steps

2-(4-Methoxyphenyl)-2H-indazole was prepared according to Song and Yee (Org. Lett. 2000, 2, 519). To a solution of N-(2-bromobenzyl)-N-(4-methoxyphenyl)hydrazine (298 mg, 0.97 mmol) in toluene (3.5 mL) were added palladium acetate (11 mg, 0.05 mmol), 1,1′-bis(diphenylphosphino)ferrocene (46 mg, 0.075 mmol) and sodium tert-butoxide (140 mg, 1.46 mmol). The vial was capped and the reaction was stirred at 90° C. overnight. After the reaction was allowed to cool, it was filtered through a pad of silica and concentrated to give the desired product. The reaction was assumed to be quantitative. LC-MS (C14H12N2O calculated 224) m/z 225 (M+H).

Provenance & Evidence