Allyl bromide → HCID 23444834, compound

HRID 1840939Notes

Reaction equation

HRID 1840939 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][O:23][C:24]3[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=3[C:26]([OH:28])=[O:27])[CH2:17][CH2:16]2)=[CH:7]1.[CH2:33](Br)[CH:34]=[CH2:35]>CN(C=O)C>[CH2:35]([O:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][O:23][C:24]3[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=3[C:26]([OH:28])=[O:27])[CH2:19][CH2:20]2)=[CH:7]1)[CH:34]=[CH2:33]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 23444865HCID 23444865, compound

Product 1

HCID 23444834HCID 23444834, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
60 °C

Procedure

To a suspension of 0.012 g (0.04 mmol) of a dispersion of 60% NaH in 0.5 mL of DMF, a solution of 0.042 g (0.01 mmol)of 2-(2-{4-[1-(2-hydroxy-ethyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoic acid in 0.5 mL of DMF was added. After stirring at room temperature for 30 minutes as solution of 0.014 g (0.12 mmol) of allyl bromide in 0.3 mL of DMF was added. The crude mixture was stirred at room temperature for 15 hours. The solvent was evaporated at reduced pressure and the crude mixture was dissolved in 1 mL of ethanol. 0.2 mL of an aqueous 2N NaOH solution were added and the mixture was heated at 60° C. for 3 hours. The solvent was removed under reduced pressure and after addition of 1 mL of water, the mixture was neutralised with 2N HCl and extracted with chloroform. The crude was purified by chromatography over silica gel affording 0.015 g (33% of yield) of the desired product.

Workup

  1. additionwas added
  2. customThe solvent was evaporated at reduced pressure
  3. dissolutionthe crude mixture was dissolved in 1 mL of ethanol
  4. addition0.2 mL of an aqueous 2N NaOH solution were added
  5. customThe solvent was removed under reduced pressure
  6. additionafter addition of 1 mL of water
  7. extractionextracted with chloroform
  8. customThe crude was purified by chromatography over silica gel affording 0.015 g (33% of yield) of the desired product

Sources & evidence

ORD record
ord-cf95811bb52f4b4d9642fd7f47e28972
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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