反应 #49877

反应方程式

5-Methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide

sodium hydride

chloromethyl methyl ether

→

5-methoxy-1-methoxymethyl-3-(1-methylethoxy)-1H-indole-2-carboxamide

收率 31.8%

溶剂

ethyl acetate

dimethylformamide

dimethylformamide

反应条件

后处理

1. 1
   洗涤washed with brine
2. 2
   干燥The organic layer is dried over MgSO4
3. 3
   过滤Filtration
4. 4
   浓缩followed by concentration in vacuo and subsequent chromatography
5. 5
   洗涤eluting with 1:1 ethyl acetate

实验过程

5-Methoxy-3-(1-methylethoxy)-1H-indole-2-carboxamide (106 mg, 0.43 mmol) in 4 mL of dimethylformamide is added to a suspension of sodium hydride (60% by weight) (30 mg, 0.75 mol) in 2 mL of dimethylformamide. After 1 hour chloromethyl methyl ether (60 μL, 0.79 mmol) is added, and the solution is stirred at room temperature overnight. The reaction mixture is diluted with ethyl acetate and washed with brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and subsequent chromatography eluting with 1:1 ethyl acetate:hexane gives 40 mg of 5-methoxy-1-methoxymethyl-3-(1-methylethoxy)-1H-indole-2-carboxamide. An analytical sample was obtained by recrystallization from ethyl acetate:hexane; mp 145°-147° C.

来源