Reacción #49877

Ecuación de reacción

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

Rendimiento 31.8%

Disolventes

ethyl acetate

dimethylformamide

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with brine
2. 2
   SecadoThe organic layer is dried over MgSO4
3. 3
   FiltraciónFiltration
4. 4
   Concentraciónfollowed by concentration in vacuo and subsequent chromatography
5. 5
   Lavadoeluting with 1:1 ethyl acetate

Procedimiento

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.

Fuente