Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:23])[C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=[O:5].[H-].[Na+].[CH3:26]I>CN(C)C=O>[CH3:1][O:2][C:3](=[O:23])[C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:13]=2)[N:8]([CH3:26])[CH:7]=1)=[O:5]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A 0° C. suspension of (6-benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester (2.70 g, 8.73 mmol) in dimethylformamide (25 mL) is treated with sodium hydride (437 mg, 10.9 mmol). The mixture is stirred at 0° C. for 20 minutes. Methyl iodide (1.00 mL; 16.1 mmol) is added. The reaction mixture is stirred at 0° C. for 30 minutes and quenched with water (100 mL). The mixture is extracted with EtOAc (50 mL×2). The combined organic layers are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by flash chromatography eluting with 60% EtOAc/Hexanes. The appropriate fractions are combined and concentrated under reduced pressure to afford the title compound (0.68 g, 24%). ES.MS m/e 324.0 (M+1).
Aufarbeitung
- stirringThe reaction mixture is stirred at 0° C. for 30 minutes
- customquenched with water (100 mL)
- extractionThe mixture is extracted with EtOAc (50 mL×2)
- dry with materialThe combined organic layers are dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product is purified by flash chromatography
- washeluting with 60% EtOAc/Hexanes
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-1f922edc966447e9852169d0bed6bd28
- Quelldatensatz
- uspto-grants-2011_01
- Patentnummer
- US07863302B2
Verknüpfte Notizen
Wird geladen…