Reacción #8410

Ecuación de reacción

NaH

4-bromoindole

triisopropylsilyl chloride

→

title compound

Rendimiento 63.0%

4-Bromo-1-(tri-isopropylsilyl)-1H-indole

Rendimiento 63.0%

Disolventes

CH2Cl2

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with water
2. 2
   FiltraciónThe insoluble material was filtered off
3. 3
   Otrothe solvent was removed
4. 4
   OtroPurification by column chromatography (SiO2, CH2Cl2/heptane 1:4)

Procedimiento

The NaH 60% dispersion in oil (0.94 g, 23.4 mmol) was added to a solution of 4-bromoindole (3.07 g, 15.6 mmol) and triisopropylsilyl chloride (3.62 g, 18.8 mmol) in CH2Cl2 (50 mL) and DMF (2 mL). The reaction was stirred at room temperature for 1 h and quenched with water. The insoluble material was filtered off and the solvent was removed. Purification by column chromatography (SiO2, CH2Cl2/heptane 1:4) yielded 3.44 g (63%) of the title compound: 1H NMR (CDCl3) δ 7.42–6.63 (m, 5 H), 1.66 (sept, J=8 Hz, 3 H), 1.10 (d, J=8 Hz, 18H; MS (ESI) 354.4 (M+H)+; Purity (HPLC) >95%.

Fuente