Réaction #1751155

Équation de réaction

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

3-amino-2-chloro-6-methylphenol

potassium carbonate

→

title compound

Rendement 64.1%

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

Rendement 64.1%

Solvants

N,N-dimethylformamide

water

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source