Ethyl bromoacetate → [6-(tert-Butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester

HRID 915389Notes

Reaction equation

HRID 915389 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24]([O:26][C:27](=[O:30])[CH2:28]Br)[CH3:25]>CN(C=O)C>[CH2:24]([O:26][C:27](=[O:30])[CH2:28][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:16])[CH:15]=2)[CH:11]=[CH:12]1)[CH3:25]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 222508166-((tert-butyldimethylsilyl)oxy)-1H-indole

Product 1

HCID 68821689[6-(tert-Butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl esterYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice cold solution of 6-(tert-butyl-dimethyl-silanyloxy)-1H-indole (1 g, 4.04 mmol) and cesium carbonate (1.45 g, 4.45 mmol) in DMF (10 ml) under an argon atmosphere was added bromo-acetic acid ethyl ester (490 μl, 4.45 mmol). The mixture was naturally warmed to room temperature, stirred for 14 h, poured onto 1 N HCl/ice water 1/1 and extracted two times with ethyl acetate. The combined organic layers were washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, heptane/AcOEt) to give 1.2 g (3.6 mmol, 89%) of the title compound as yellow oil.

Workup

  1. extractionextracted two times with ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-3dfc4e38ae334a2e88b4aaba76ead05f
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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