3-Methoxy-2-pyridone → HCID 59586725, Verbindung
Reaktionsgleichung
[CH3:1][O:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].[F:16][CH:17]([F:29])[O:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1F>CS(C)=O.ClCCl>[F:16][CH:17]([F:29])[O:18][C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]1=[O:9]Komponenten
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
302 mg (2.41 mmol) of 3-methoxypyridone are dissolved in 8.2 ml of anhydrous dimethyl sulfoxide and admixed with 325 mg (2.89 mmol) of potassium tert-butoxide. After 30 min, 500 mg (2.41 mmol) of 2-(difluoromethoxy)-1-fluoro-4-nitrobenzene are added and the mixture is heated to 80° C. for 20 h. The reaction solution is diluted with dichloromethane and washed with water and 1N hydrochloric acid. After the organic phase has been dried over sodium sulfate, it is filtered and concentrated to dryness under reduced pressure. The residue is dissolved in dimethyl sulfoxide and purified by preparative HPLC with a water/acetonitrile gradient. The product fractions are combined and concentrated to dryness under reduced pressure. This affords 207 mg (28% of theory) of the desired product.
Aufarbeitung
- washwashed with water and 1N hydrochloric acid
- dry with materialAfter the organic phase has been dried over sodium sulfate, it
- filtrationis filtered
- concentrationconcentrated to dryness under reduced pressure
- dissolutionThe residue is dissolved in dimethyl sulfoxide
- custompurified by preparative HPLC with a water/acetonitrile gradient
- concentrationconcentrated to dryness under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-613ac57eb69c41b59e8642ec5330dd1f
- Quelldatensatz
- uspto-grants-2012_06
- Patentnummer
- US08198267B2
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