5-Bromoindole → 5-Bromo-1-(triisopropylsilyl)-1H-indole

HRID 384854Notes

Reaction equation

HRID 384854 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH:11]([Si:14](Cl)([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])([CH3:13])[CH3:12]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:14]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:11]([CH3:13])[CH3:12])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 249055-BromoindoleHCID 139400Triisopropylsilyl chloride

Product 1

HCID 27946525-Bromo-1-(triisopropylsilyl)-1H-indoleYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-Bromoindole (2.5 g, 12.75 mmol) was dissolved in tetrahydrofuran (THF; 50 mL) and cooled to 0° C. and Sodium Hydride NaH (920 mg, 23 mmol, 60%) was added in portions. The mixture was allowed to warm to RT with stirring for 1 hour. The reaction mixture was again cooled to 0° C. and triisopropylsilyl chloride (TIPSCl; 2.78 mL, 13.1 mmol) was added dropwise. The mixture was allowed to warm to room temperature and was stirred overnight. The mixture was washed with 2.0 N H3PO4, and the organic layer was dried over MgSO4, filtered and evaporated. The residue was purified by flash silica chromatography (100% Hexanes) to give compound 8 as an oil (4.3 g; 96% yield; M+1=353.4)

Workup

  1. temperatureto warm to RT
  2. temperatureThe reaction mixture was again cooled to 0° C.
  3. temperatureto warm to room temperature
  4. stirringwas stirred overnight
  5. washThe mixture was washed with 2.0 N H3PO4
  6. dry with materialthe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash silica chromatography (100% Hexanes)

Sources & evidence

ORD record
ord-48265d5876a04f839053233040a6a09a
Source dataset
uspto-grants-2013_02
Patent number
US08367828B2

Reaction notes

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