Reaction #48833

Reaction equation

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

Yield 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

Yield 84.5%

Solvents

ethyl acetate

acetonitrile

Conditions

Workup

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

Procedure

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