Reaktionsgleichung
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][C:3]=1[CH3:16].[H-].[Na+].Cl[CH2:20][C:21]#[N:22].O>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]2[CH2:20][C:21]#[N:22])=[CH:4][C:3]=1[CH3:16]Komponenten
6
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A solution of ethyl 6-chloro-5-methylindole-2-carboxylate (1.5 g, 6.3 mmol) in DMF (30 mL) was added dropwise to a stirred suspension of sodium hydride (60%, 0.39 g, 10 mmol) in DMF (20 mL) at room temperature under Ar. The reaction was then cooled to 0° C. and stirred for 45 min then chloroacetonitrile (0.81 mL, 13 mmol) was added in one portion. The reaction was heated to 75° C. and stirred for 1 h. After allowing to cool to room temperature the mixture was poured into water (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (1×100 mL), dried (magnesium sulfate), filtered and the solvent removed under vacuum to leave the crude product which was used immediately.
Aufarbeitung
- temperatureThe reaction was heated to 75° C.
- stirringstirred for 1 h
- temperatureto cool to room temperature the mixture
- extractionextracted with ethyl acetate (3×100 mL)
- washThe combined organic extracts were washed with brine (1×100 mL)
- dry with materialdried (magnesium sulfate)
- filtrationfiltered
- customthe solvent removed under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-f85ef82ab3724da99f2d114d364ba6a9
- Quelldatensatz
- uspto-grants-2006_12
- Patentnummer
- US07145009B2
Verknüpfte Notizen
Wird geladen…