Diethyl Ether → 4-bromo-1-(triisopropylsilyl)-1H-indole
Reaktionsgleichung
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14].CCOCC>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of the indole of Step 1 (8.9 g, 45 mmol) in DMF (150 mL) at 0° C. was added portionwise NaH (2.2 g, 55 mmol, 60% in oil). The reaction mixture was stirred for 30 minutes at 0° C. and triisopropylsilyl chloride (10.5 g, 55 mmol) was added. The reaction mixture was stirred for 30 minutes and 400 mL of Et2O was added. The reaction was quenched with saturated aqueous NH4Cl and extracted with Et2O. The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 100% Hexanes to provide 16 g of the title compound as a white solid.
Aufarbeitung
- stirringThe reaction mixture was stirred for 30 minutes
- customThe reaction was quenched with saturated aqueous NH4Cl
- extractionextracted with Et2O
- washThe combined organic layers were washed with water and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography
- washeluted with 100% Hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-36ef51cd022b43afb9d6cd37cf4e78ff
- Quelldatensatz
- uspto-grants-2006_12
- Patentnummer
- US07144913B2
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