Cesium carbonate → [6-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester
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+].[C:24]([O:28][C:29](=[O:32])[CH2:30]Br)([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C>[C:24]([O:28][C:29](=[O:32])[CH2:30][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)([CH3:27])([CH3:26])[CH3:25]Participants
5
Procedure
To an ice cold solution of 6-(tert-butyl-dimethyl-silanyloxy)-1H-indole (13 g, 52.5 mmol) and cesium carbonate (18.8 g, 57.8 mmol) in DMF (130 ml) under an argon atmosphere was added bromo-acetic acid tert-butyl ester (8.5 ml, 57.8 mmol). The mixture was naturally warmed to room temperature, stirred for 14 h, poured onto 2 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 14.3 g (39.6 mmol, 75%) of the title compound as yellow oil.
Workup
- extractionextracted two times with ethyl acetate
- washThe combined organic layers were washed with water
- dry with materialdried over sodium sulfate
- customThe solvent was removed under reduced pressure
- customthe residue purified by column chromatography (silica gel, heptane/AcOEt)
Sources & evidence
- ORD record
- ord-1929db2137ea48d3a1d8d763875bd9c4
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265149B2
Reaction notes
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