Sodium hydride → 5-Bromo-1-(triisopropylsilyl)-1H-indole

HRID 1683281Notes

Reaction equation

HRID 1683281 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Na].[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[CH:17]2.[H-].[Na+]>CN(C)C=O.ClCCl>[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])[CH:18]=[CH:17]2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 249055-BromoindoleHCID 139400Triisopropylsilyl chlorideHCID 5360545Sodium

Product 1

HCID 27946525-Bromo-1-(triisopropylsilyl)-1H-indole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Triisopropylsilyl chloride (6.87 g) was added to the sodium salt prepared from 5bromoindole (6.35 g) and sodium hydride (1.71 g, 50% suspension in oil) in dimethylformamide (32 ml) and the mixture was stirred at room temperature for 2 hours then poured into ice water (150 ml). The crude intermediate obtained by evaporation of the dichloromethane extract was column chromatographed (silica gel, 40°-60° C. petroleum ether) to give 5-bromo-1-triisopropylsilylindole isolated as an oil.

Workup

  1. extractionextract
  2. customchromatographed (silica gel, 40°-60° C. petroleum ether)

Sources & evidence

ORD record
ord-dc3df8ed7c324d639c62b9f341b75cc4
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

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