Reaktion #1751155

Reaktionsgleichung

N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

3-amino-2-chloro-6-methylphenol

potassium carbonate

→

title compound

Ausbeute 64.1%

N-[6-(3-amino-2-chloro-6-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Ausbeute 64.1%

Lösungsmittel

N,N-dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling the mixture to room temperature
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with 5% aqueous sodium hydrogencarbonate solution and saturated brine
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Filtrationfiltrated
6. 6
   SonstigeThe solvent was evaporated under reduced pressure
7. 7
   Sonstigethe residue was purified by NH silica gel column chromatography (ethyl acetate/hexane=50/50→80/20)
8. 8
   Sonstigeprecipitated from methanol/diisopropyl ether

Vorschrift

To a solution of N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide (2.0 g, 6.1 mmol) in N,N-dimethylformamide (20 mL) were added 3-amino-2-chloro-6-methylphenol (1.9 g, 12 mmol) and potassium carbonate (2.1 g, 15 mmol), and the mixture was stirred at 140° C. for 12 hr. After cooling the mixture to room temperature, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate/hexane=50/50→80/20) and precipitated from methanol/diisopropyl ether to give the title compound (1.4 g, 64%) as a pale-yellow powder.

Quelle