Reaktion #48833

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 84.5%

Lösungsmittel

ethyl acetate

acetonitrile

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle