تفاعل #49877

معادلة التفاعل

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

المردود 31.8%

المذيبات

ethyl acetate

dimethylformamide

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with brine
2. 2
   تجفيفThe organic layer is dried over MgSO4
3. 3
   ترشيحFiltration
4. 4
   تركيزfollowed by concentration in vacuo and subsequent chromatography
5. 5
   غسيلeluting with 1:1 ethyl acetate

الإجراء التجريبي

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.

المصدر