Reacción #48833

Ecuación de reacción

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

Rendimiento 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

Rendimiento 84.5%

Disolventes

ethyl acetate

acetonitrile

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente