Reacción #8192

Ecuación de reacción

[2-(7-hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

bromoacetonitrile

K2CO3

→

[2-(7-cyanomethoxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

Rendimiento 86.5%

Disolventes

2-butanone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais heated to reflux
2. 2
   Temperaturato cool
3. 3
   Filtraciónis filtered through celite
4. 4
   ConcentraciónThe filtrate is concentrated to an oil which
5. 5
   Otrois purified by flash chromatography with CH2Cl2

Procedimiento

A mixture of [2-(7-hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (15.55 g, 51.1 mmol), bromoacetonitrile (10.7 mL, 153 mmol), K2CO3 (17.78 g, 128.6 mmol) and 2-butanone is heated to reflux. After 1 hour the mixture is allowed to cool and is filtered through celite. The filtrate is concentrated to an oil which is purified by flash chromatography with CH2Cl2 followed by 5% ethyl acetate/CH2Cl2 to give 15.18 g of [2-(7-cyanomethoxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (86%). MS (ES−) m/z 342.

Fuente