Reaktion #420907

Reaktionsgleichung

1-Benzyl-3-chloro-5-methoxypyridazin-4(1H)-one

potassium carbonate

1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

→

title compound

Ausbeute 77.7%

1-benzyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

Ausbeute 77.7%

Lösungsmittel

water

toluene

water

sodium hydrogen carbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux under a nitrogen atmosphere for 24 hr
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   TrocknenThe extract was dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenthe filtrate was concentrated
6. 6
   Sonstigethe residue was recrystallized from ethyl acetate/hexane

Vorschrift

1-Benzyl-3-chloro-5-methoxypyridazin-4(1H)-one (13.6 g), 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (22.0 g), potassium carbonate (51.0 g) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (1.92 g) were suspended in toluene (330 mL) and water (33.0 mL), and the mixture was heated under reflux under a nitrogen atmosphere for 24 hr. The reaction mixture was cooled to room temperature, diluted with water and saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated, and the residue was recrystallized from ethyl acetate/hexane to give the title compound (15.1 g).

Quelle