반응 #48833

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Trimethylsilyl iodide

3-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(1,2,4-oxadiazol-3-yl)phenoxy]benzamide

→

title compound

수율 84.5%

3-[(1S)-2-Hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(1,2,4-oxadiazol-3-yl)phenoxy]benzamide

수율 84.5%

용매

ethyl acetate

acetonitrile

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후처리

1. 1
   기타quenched by the addition of saturated aqueous sodium bicarbonate (20 mL)
2. 2
   세척The organic phase was washed with saturated aqueous thiosulphate solution (20 mL)
3. 3
   건조dried (MgSO4)
4. 4
   기타The volatiles were removed under reduced pressure
5. 5
   기타the resulting oil purified by chromatography on silica
6. 6
   세척eluting with 0-100% ethyl acetate in iso-hexane

실험 절차

Trimethylsilyl iodide (0.062 mL, 0.434 mmol) was added to a solution of 3-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(1,2,4-oxadiazol-3-yl)phenoxy]benzamide (78 mg, 0.174 mmol) in acetonitrile (2 mL) and the reaction mixture allowed to stir at RT for 18 hours. The reaction was diluted with ethyl acetate (15 mL) and quenched by the addition of saturated aqueous sodium bicarbonate (20 mL). The organic phase was washed with saturated aqueous thiosulphate solution (20 mL) and dried (MgSO4). The volatiles were removed under reduced pressure and the resulting oil purified by chromatography on silica, eluting with 0-100% ethyl acetate in iso-hexane, to give the title compound as a colourless solid (64 mg).

출처