Reaktion #661494

Reaktionsgleichung

5-Bromoindole

NaH

triisopropylsilyl chloride

→

product 47

Ausbeute 76.0%

5-bromo-1-triisopropylsilyl-1H-indole

Ausbeute 76.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was again cooled to 0° C.
2. 2
   Temperaturto warm to room temperature
3. 3
   workup.STIRRINGwas stirred overnight
4. 4
   SonstigeThe solvent was evaporated under reduced pressure
5. 5
   Sonstigetriturated with ethyl acetate (100 ml)
6. 6
   WaschenThe organic layer was washed with brine (50 ml)
7. 7
   Trocknendried over Na2SO4
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe compound was purified by flash column chromatography

Vorschrift

5-Bromoindole (1.4 gm, 7.14 mmol) was dissolved in dry THF (50 ml) and cooled to 0° C., which was followed by the addition of NaH (0.34 g, 14.28 mmol) portion wise. The reaction mixture was allowed to stir at room temperature for 1 h. The reaction mixture was again cooled to 0° C. and triisopropylsilyl chloride (1.78 g, 9.28 mmol) was added drop wise. The mixture was allowed to warm to room temperature and was stirred overnight. The solvent was evaporated under reduced pressure and triturated with ethyl acetate (100 ml). The organic layer was washed with brine (50 ml) and dried over Na2SO4 and evaporated. The compound was purified by flash column chromatography using pure hexanes to afford colorless oily product 47 (1.90 g, 76%). 1H NMR (400 MHz, CDCl3) δ 1.13 (d, 18H, J=8.0 Hz), 1.63-1.71 (m, 3H), 6.56 (d, 1H, J=3.2 Hz), 7.20-7.25 (m, 2H), 7.37 (d, 1H, J=8.8 Hz), 7.74 (d, 1H, J=2.0 Hz).

Quelle