Ethyl bromoacetate → [7-(tert-Butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester

HRID 751214Notes

Reaction equation

HRID 751214 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2)([CH3:4])([CH3:3])[CH3:2].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][N:14]1[C:15]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:16])[CH:12]=[CH:13]1)[CH3:24]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 571109747-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indole

Product 1

HCID 68824002[7-(tert-Butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In analogy to the procedure described in example 6 b], 7-(tert-butyl-dimethyl-silanyloxy)-1H-indole (EP 206225 A2) was reacted with ethyl bromoacetate in the presence of cesium carbonate in acetonitrile to give the title compound as colorless liquid.

Sources & evidence

ORD record
ord-e6325e077dd348f6ae14e2fa726508fb
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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