Potassium Carbonate → Methyl 2-(5-chloro-2-methyl-1H-indol-1-yl)acetate
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]([CH3:15])=[CH:5]2.[C:16](=O)([O-])[O-].[K+].[K+].BrCC(OC)=O>CN(C)C=O>[CH3:16][O:13][C:12](=[O:14])[CH2:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[CH3:15]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A mixture of (5-chloro-2-methylindol-1-yl)acetic acid (25 g), potassium carbonate (100 g) and N,N-dimethylformamide (220 mL) was treated dropwise with methyl bromoacetate (37 g), and the resulting mixture was stirred at 60° C. for 2 days. The mixture was cooled to room temperature and partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic solution was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and pentane (1:10 to 1:0 by volume) to afford the title compound as a white solid (27 g).
Aufarbeitung
- temperatureThe mixture was cooled to room temperature
- custompartitioned between water and ethyl acetate
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe combined organic solution was washed with saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel
- washeluting with a mixture of dichloromethane and pentane (1:10 to 1:0 by volume)
Quellen und Nachweise
- ORD-Eintrag
- ord-c032083b613143e79790eac64e61c3d4
- Quelldatensatz
- uspto-grants-2013_03
- Patentnummer
- US08394836B2
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