Réaction #48833

Équation de réaction

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

Rendement 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

Rendement 84.5%

Solvants

ethyl acetate

acetonitrile

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source