反应详情

温度

50 °C

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.

1. customat ambient temperature
2. customovernight
3. temperatureThe medium is heated to around 50° C.
4. stirringAfter stirring for 3 hours
5. stirringAfter stirring for approximately 4 hours
6. stirringstirred at ambient temperature for about fifteen minutes
7. filtrationThe suspension is filtered through a paper
8. filtrationfilter
9. concentrationthe filtrate is concentrated under vacuum in a rotary evaporator
10. customThe reaction crude
11. washthe 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
12. dry with materialThe organic phase is dried over magnesium sulfate
13. concentrationconcentrated under vacuum in a rotary evaporator
14. customThe reaction crude
15. customis purified by flash chromatography on silica (Varian 20 g cartridge), eluent