Water → HCID 60110695, compound

HRID 1007482Notes

Reaction equation

HRID 1007482 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]([CH3:15])[CH3:14].[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17].O>C1COCC1>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21])[CH:8]=[C:7]2[CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 12137096HCID 12137096, compound

Product 1

HCID 60110695HCID 60110695, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.50 g (12.6 mmol) of 60% strength sodium hydride in paraffin oil is introduced under argon into 20 ml of THF at room temperature. A solution of 2.0 g (8.40 mmol) of 5-bromo-3-isopropyl-1H-indole (Example X) in 20 ml of THF is added dropwise and the mixture is stirred until evolution of gas can no longer be detected. 2.03 g (13.44 mmol) of tert-butyl(chloro)dimethylsilane are subsequently added dropwise. After a short reaction time a precipitate deposits. The batch is stirred for 3 h at room temperature. It is treated with 200 ml of water. The aqueous phase is extracted twice with ethyl acetate, and the combined org. phases are dried and concentrated in a rotary evaporator. The residue is chromatographed on silica gel (eluent: cyclohexane). 2.63 g (89%) of 5-bromo-1-[tert-butyl(dimethyl)silyl]-3-isopropyl-1H-indole are obtained.

Workup

  1. stirringThe batch is stirred for 3 h at room temperature
  2. extractionThe aqueous phase is extracted twice with ethyl acetate
  3. customphases are dried
  4. concentrationconcentrated in a rotary evaporator
  5. customThe residue is chromatographed on silica gel (eluent: cyclohexane)

Sources & evidence

ORD record
ord-ad22692dd0244d419999decda45f115d
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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