Reacción #52317

Ecuación de reacción

Water

Lithium hexamethyldisilazane

5-bromo-1H-indole

triisopropylsilyl chloride

→

title compound

Rendimiento 92.0%

5-Bromo-1-triisopropylsilanyl-1H-indole

Rendimiento 92.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred for 30 minutes
2. 2
   Otroto quench
3. 3
   Otrothe reaction
4. 4
   Otrothe solvent was removed under reduced pressure
5. 5
   Otroto give the crude mixture, which
6. 6
   Otrowas purified via column chromatography on silica gel (9:1 Hexane/ethyl acetate)

Procedimiento

Lithium hexamethyldisilazane [1.0 M] (44.7 mL, 44.4 mmol) was added to a solution of 5-bromo-1H-indole (7.30 g, 37.0 mmol) in tetrahydrofuran (50 mL) at room temperature. After stirring for 5 minutes, triisopropylsilyl chloride (8.62 g, 44.4 mmol) was added to reaction mixture and stirred for 30 minutes. Water was added to quench the reaction and the solvent was removed under reduced pressure to give the crude mixture, which was purified via column chromatography on silica gel (9:1 Hexane/ethyl acetate) to give the title compound in 92% yield. 1H NMR (CDCl3) δ 7.74 (d, J=1.8, 1H), 7.36 (d, J=8.8 Hz, 1H), 7.22 (m, 2H), 6.55 (d, J=3.1 Hz, 1H), 1.65 (m, 3H), 1.12 (d, J=7.5 Hz, 18H).

Fuente