Sodium hydride → HCID 68534632, compound

HRID 2108671Notes

Reaction equation

HRID 2108671 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].[CH3:16][CH:17]([Si:19](Cl)([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH3:18]>C1COCC1.CCOC(C)=O.O>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([Si:19]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:18])[CH3:16])[CH:8]=[C:7]2[CH:13]([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 12137096HCID 12137096, compound

Product 1

HCID 68534632HCID 68534632, compoundYield 67.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of NaH (509 mg, 20.16 mmol) in THF (50 ml) was added 5-bromo-3-isopropyl-1H-indole (4.55 g, 19.20 mmol). The reaction mixture was stirred at r.t. for 30 min, and TIPSCl was then added at r.t. The reaction was stirred further for 1 hr, diluted with EtOAc, and water was added to quench the reaction. The organic layer was collected and the water layer was further extracted with EtOAC once. The combined organic layer was dried over MgSO4, filtrated and concentrated. The residue was purified by column chromatography on silica gel, eluting with hexane to afford 5-bromo-3-isopropyl-1-triisopropylsilyl-1H-indole (5.1 g, 67.6%): 1H NMR (200 MHz, CDCl3): δ 7.53 (d, J=1.8 Hz, 1H), 7.13 (d, J=8.8 Hz, 1H), 6.99 (m, 1H), 6.76(s, 1H), 2.92 (m, 1H), 1.44 (m, 3H), 1.14 (d, J=6.6 Hz, 6H), 0.93 (d, J=7.4 Hz, 18H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=Hexane (1:9); Rf=0.65.

Workup

  1. stirringThe reaction was stirred further for 1 hr
  2. additionwas added
  3. customto quench
  4. customthe reaction
  5. customThe organic layer was collected
  6. extractionthe water layer was further extracted with EtOAC once
  7. dry with materialThe combined organic layer was dried over MgSO4
  8. filtrationfiltrated
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography on silica gel
  11. washeluting with hexane

Sources & evidence

ORD record
ord-e423b4f9a1dc411b8457e054ea25bd63
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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