Реакция #49877

Уравнение реакции

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

Выход 31.8%

Растворители

ethyl acetate

dimethylformamide

dimethylformamide

Условия реакции

Обработка

1. 1
   Промывкаwashed with brine
2. 2
   СушкаThe organic layer is dried over MgSO4
3. 3
   ФильтрацияFiltration
4. 4
   Концентрированиеfollowed by concentration in vacuo and subsequent chromatography
5. 5
   Промывкаeluting with 1:1 ethyl acetate

Методика

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.

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