Sodium hydride → HCID 17985412, compound

HRID 557195Notes

Reaction equation

HRID 557195 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.Br[CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C)C=O>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6764944-BromoindoleHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 17985412HCID 17985412, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (4.89 g, 122.4 mmol, 60% dispersion in mineral oil) to a solution of 4-Bromo-1H-indole (12 g, 61.2 mmol) in dimethylformamide (100 ml). Cool the reaction to 0° C. and add (2-bromo-1-(tert-butyldimethylsilyloxy)ethane (17.04 g, 67.32 mmol). Stir the reaction for 1 hour at room temperature, quench with aqueous saturated sodium bicarbonate, and extract into ethyl acetate. Combine the organic layers and wash with saturated aqueous sodium chloride, dry over magnesium sulfate. Concentrate under reduced pressure to obtain the title compound, as a clear oil.

Workup

  1. temperatureCool
  2. customthe reaction to 0° C.
  3. customthe reaction for 1 hour at room temperature
  4. customquench with aqueous saturated sodium bicarbonate
  5. extractionextract into ethyl acetate
  6. washwash with saturated aqueous sodium chloride
  7. dry with materialdry over magnesium sulfate
  8. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-f0456cc9f8e3414aa0d770bd001b1582
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

Loading…