Cesium carbonate → [6-(Tert-butyl-dimethyl-silanyloxy)-3-chloro-indol-1-yl]-acetic acid tert-butyl ester

HRID 1767979Notes

Reaction equation

HRID 1767979 reaction equation
[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([Cl:16])=[CH:12][NH:13]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[C:19]([O:23][C:24](=[O:27])[CH2:25]Br)([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:19]([O:23][C:24](=[O:27])[CH2:25][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])([CH3:18])[CH3:17])[CH:15]=2)[C:11]([Cl:16])=[CH:12]1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 236145106-{[tert-Butyl(dimethyl)silyl]oxy}-3-chloro-1H-indole

Product 1

HCID 69283059[6-(Tert-butyl-dimethyl-silanyloxy)-3-chloro-indol-1-yl]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedure described in example 1 b], 6-(tert-butyl-dimethyl-silanyloxy)-3-chloro-1H-indole was reacted with bromo-acetic acid tert-butyl ester in the presence of cesium carbonate in DMF to obtain [6-(tert-butyl-dimethyl-silanyloxy)-3-chloro-indol-1-yl]-acetic acid tert-butyl ester as yellow oil.

Sources & evidence

ORD record
ord-937796f1d19f494794a671b35c2bfb57
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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