Methanol → 3-styryl-1H-indazol-5-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 652 mg of 5-benzyloxy-3-((E)-styryl)-1H-indazole in 60 ml of acetonitrile is stirred under argon. 1.13 ml of iodotrimethylsilane are added dropwise under an inert atmosphere. The suspension is stirred at approximately 50° C. for 3 hours and then at ambient temperature overnight. The medium is heated to around 50° C. and then 1.2 ml of iodotrimethylsilane are added. After stirring for 3 hours, 0.8 ml of iodotrimethylsilane is added. After stirring for approximately 4 hours, the medium is treated with 10 ml of methanol and stirred at ambient temperature for about fifteen minutes. The suspension is filtered through a paper filter and the filtrate is concentrated under vacuum in a rotary evaporator. The reaction crude is taken up in 50 ml of ethyl acetate and the organic phase is washed with 2×50 ml of a sodium thiosulfate solution, 2×50 ml of a saturated sodium bicarbonate solution, and 50 ml of a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and then concentrated under vacuum in a rotary evaporator. The reaction crude is purified by flash chromatography on silica (Varian 20 g cartridge), eluent: ethyl acetate/cyclohexane gradient 5:95 to 35:65 to obtain 265.4 mg of 3-styryl-1H-indazol-5-ol.

Provenance & Evidence