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

HRID 2100436Notes

Reaction equation

HRID 2100436 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 (TIPSCI; 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 NH3PO4, 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 NH3PO4
  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-e5587fac554649e3aa19e7c3017d65f4
Source dataset
uspto-grants-2009_08
Patent number
US07572806B2

Reaction notes

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