反应 #48853

反应方程式

Iodotrimethylsilane

3-hydroxy-5-[(1R)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

potassium carbonate

sodium thiosulphate

→

desired compound

收率 64.0%

3-Hydroxy-5-[(1R)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

收率 64.0%

溶剂

Methanol

acetonitrile

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture stirred for 20 mins
2. 2
   其他The acetonitrile was removed in vacuo and water (50 mL)
3. 3
   workup.ADDITIONadded
4. 4
   萃取extracted into ethyl acetate (3×100 mL)
5. 5
   洗涤the combined extracts washed with brine (50 mL)
6. 6
   干燥dried (MgSO4)
7. 7
   其他evaporated to a residue which
8. 8
   其他was chromatographed on silica
9. 9
   洗涤eluting with a gradient of 0-50% methanol in ethyl acetate

实验过程

Iodotrimethylsilane (6.64 mL, 47 mmol) was added to a solution of 3-hydroxy-5-[(1R)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (2.86 g, 9.38 mmol) in acetonitrile (120 mL) and the resultant mixture stirred for 24 hours. Methanol (30 mL) was added and the mixture stirred for 30 minutes, saturated potassium carbonate (30 mL) and saturated sodium thiosulphate (30 mL) were then added and the mixture stirred for 20 mins. The acetonitrile was removed in vacuo and water (50 mL) added. The mixture was adjusted to pH4 with 1M hydrochloric acid, extracted into ethyl acetate (3×100 mL) and the combined extracts washed with brine (50 mL), dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with a gradient of 0-50% methanol in ethyl acetate, to give the desired compound (1.75 g).

来源