Sodium hydride → 6-bromo-1-(triisopropylsilyl)-1H-indole

HRID 2084058Notes

Reaction equation

HRID 2084058 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 6764936-Bromoindole

Product 1

HCID 129912436-bromo-1-(triisopropylsilyl)-1H-indoleYield 23.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 6-Bromoindole (1 g, 5 mmol) in DMF (3 ml) was added to a suspension of NaH (134.7 mg, 5.6 mmol) in DMF (98 ml) at 0° C. and stirred for 15 mins. Triisopropylsilyl chloride (1.082 g, 5.6 mmol) was added dropwise, and the reaction mixture stirred for 2 h before being poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, concentrated in vacuo and the crude product passed through a silica gel column, eluting with hexanes, to give the title compound (406.7 mg, 23%) as a colourless oil.

Workup

  1. stirringthe reaction mixture stirred for 2 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated in vacuo
  5. washeluting with hexanes

Sources & evidence

ORD record
ord-cfb130646e9c41a2a652f9f92fef2298
Source dataset
uspto-grants-2004_04
Patent number
US06716837B1

Reaction notes

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