Reacción #442870

Ecuación de reacción

ethyl bromoacetate

ethyl 7-nitro-1H-indole-2-carboxylate

sodium hydride

→

ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate

Rendimiento 78.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe resulting mixture was stirred at 50°-60° C. for 4 hours
2. 2
   TemperaturaThe reaction mixture was cooled to room temperature
3. 3
   Extracciónfollowed by extraction with ethyl acetate (three times)
4. 4
   LavadoThe organic layer was washed with water
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   Otrothe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95)

Procedimiento

To a solution of ethyl 7-nitro-1H-indole-2-carboxylate (2.00 g, 8.45 mmol) in N,N-dimethylformamide (50 ml) was added 60% sodium hydride (0.34 g, 8.54 mmol), and the reaction mixture was stirred at room temperature until it became transparent. Then, ethyl bromoacetate (1.43 g, 8.54 mmol) was added and the resulting mixture was stirred at 50°-60° C. for 4 hours. The reaction mixture was cooled to room temperature and poured into ice water, followed by extraction with ethyl acetate (three times). The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95) to obtain ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate (2.11 g).

Fuente