Sodium hydride → Diethyl-carbamic acid 1-(tert-butyl-dimethyl-silanyl)-1H-indol-5-yl ester

HRID 45142

Reaktionsgleichung

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11](=[O:17])[N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C1COCC1>[C:21]([Si:24]([CH3:26])([CH3:25])[N:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11](=[O:17])[N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)([CH3:23])([CH3:22])[CH3:20]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Diethyl-carbamic acid 1H-indol-5-yl ester (5.72 g, 24.6 mmol) is dissolved in THF (200 mL) and cooled to 0° C. The flask is purged with nitrogen and then 60% NaH (1.1 g, 27.5 mmol) is added and the mixture stirred in aen ice bath for 30 minutes. At that point TBDMSCl (0.210 g, 1.39 mmol) is added and the reaction is allowed to stir overnight (14 hours). The reaction is quenched with a saturated solution of ammonium chloride and the mixture is diluted with ethyl acetate and water. The organic layer is removed, dried (sodium sulfate) and concentrated to obtain the title compound as an oil that is used without further purification. MS (ESI) m/z 347.21 (M+1).

Aufarbeitung

customThe flask is purged with nitrogen
stirringto stir overnight (14 hours)
customThe reaction is quenched with a saturated solution of ammonium chloride
additionthe mixture is diluted with ethyl acetate and water
customThe organic layer is removed
dry with materialdried (sodium sulfate)
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-ae0d6c36f9864a498c0350d18282f7cc
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08541432B2

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