Ethyl bromoacetate → ethyl (4-{[tert-butyl(dimethyl)silyl]oxy}-1H-indol-1-yl)acetate

HRID 890458Notes

Reaction equation

[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([O:20][C:21](=[O:24])[CH2:22]Br)[CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:18]([O:20][C:21](=[O:24])[CH2:22][N:11]1[C:12]2[C:8](=[C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:16])[CH:15]=[CH:14][CH:13]=2)[CH:9]=[CH:10]1)[CH3:19]

Participants

Reactant 3

HCID 7748Ethyl bromoacetate

HCID 10796Cesium carbonate

HCID 115939764-(t-Butyldimethylsilyloxy)indole

Product 1

HCID 68822793ethyl (4-{[tert-butyl(dimethyl)silyl]oxy}-1H-indol-1-yl)acetate

Procedure

In analogy to the procedure described in example 6 a], 4-(tert-butyl-dimethyl-silanyloxy)-1H-indole (EP 206225 A2) was reacted with bromo-acetic acid ethyl ester in the presence of cesium carbonate to obtain the title compound as yellow oil.

Sources & evidence

ORD record: ord-a58b05aae28e4e858b89e11fa3033b88
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995263B2

Reaction notes

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