Reacción #339782

Ecuación de reacción

diethyl zinc

1-ethyl-6-vinyloxy-1H-indole-3-carbonitrile

chloroiodomethane

NH4Cl

ammonium hydroxide

→

6-cyclopropoxy-1-ethyl-1H-indole-3-carbonitrile

Rendimiento 45.7%

Disolventes

1,2-dichloroethane

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is warmed to 20-25° C. for 20 min.
2. 2
   Temperaturacooled back to 0° C
3. 3
   OtroAfter the phases are separated
4. 4
   Extracciónthe aqueous phase is back-extracted with ethyl acetate (10 mL)
5. 5
   LavadoThe combined organic phases are washed with saturated NH4Cl (10 mL)
6. 6
   Secadodried over MgSO4
7. 7
   Concentraciónthe solution is concentrated
8. 8
   Otrothe product is purified by chromatography
9. 9
   Lavadoeluting with 15-30% ethyl acetate/hexanes

Procedimiento

Via a syringe, diethyl zinc is added to a mixture of 1-ethyl-6-vinyloxy-1H-indole-3-carbonitrile (288.1 mg, 1.36 mmol), chloroiodomethane (268.9 mg, 1.53 mmol) and 5 ml of 1,2-dichloroethane over a period of 10 min, maintaining the temperature at −10° C. The mixture is warmed to 20-25° C. for 20 min., and then cooled back to 0° C. Saturated NH4Cl (15 mL), concentrated ammonium hydroxide (15 mL), and ethyl acetate (15 mL) are added in sequence at this temperature, and stirred for 10 min. After the phases are separated, the aqueous phase is back-extracted with ethyl acetate (10 mL). The combined organic phases are washed with saturated NH4Cl (10 mL), dried over MgSO4 and then the solution is concentrated and the product is purified by chromatography, eluting with 15-30% ethyl acetate/hexanes to afford 140.5 mg (45.7% yield) of 6-cyclopropoxy-1-ethyl-1H-indole-3-carbonitrile as a yellow solid.

Fuente