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

HRID 1887637

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-2178d3aa45da4e099d5baf0fa5e397fb
Quelldatensatz: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08501756B2

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