Reacción #8432

Ecuación de reacción

MgSO4

NaH

5-Bromoindole

triisopropylsilyl chloride

→

5-Bromo-1-triisopropylsilyl-indole

Rendimiento 85.0%

Disolventes

DMF

water

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 3 h
2. 2
   FiltraciónThe mixture was filtered
3. 3
   Concentraciónconcentrated
4. 4
   OtroThe product was obtained as a pale yellow oil (5.96 g, 17 mmol; yield 85%)

Procedimiento

5-Bromoindole (3.92 g; 20 mmol) was dissolved in DCM (100 mL) and DMF (1 mL). NaH (0.88 g, 22 mmol; 60% in oil) was added to the cooled solution. After stirring for 15 minutes, triisopropylsilyl chloride (3.86 g, 20 mmol) was added dropwise to the reaction mixture. After 3 h, water (1 mL) was added, followed by MgSO4. The mixture was filtered and concentrated and the residue put through a silica column with hexane as eluent. The product was obtained as a pale yellow oil (5.96 g, 17 mmol; yield 85%). 1H NMR (CDCl3) δ 1.13 (18 H, d, J=8), 1.67 (3 H, m), 6.55 (1 H, d, J=3), 7.21 (1 H, dd, J=9, 2), 7.24 (1 H, d, J=3), 7.36 (1 H, d, J=9) and 7.74 (1 H, d, J=2).

Fuente