Réaction #167891

Équation de réaction

ethyl 4-[2-(4-fluorophenyl)-6-(4-methylpiperazin-1-yl)imidazo[1,2-b]pyridazin-3-yl]-4H-pyridine-1-carboxylate

ortho-chloranil

sodium hydroxide

→

crystals

Rendement 56.0%

2-(4-Fluorophenyl)-6-(4-methylpiperazin-1-yl)-3-pyrid-4-ylimidazo[1,2-b]pyridazine

Rendement 56.0%

Solvants

toluene

toluene

Conditions de réaction

Traitement

1. 1
   AutreAfter reaction for 6 hours
2. 2
   Extractionthe product is extracted with ethyl acetate
3. 3
   LavageThe organic phase is washed with saturated aqueous sodium chloride solution
4. 4
   Séchagedried over sodium sulfate
5. 5
   Autrethe solvent is evaporated off under reduced pressure
6. 6
   Autre1.2 g of solid are thus recovered
7. 7
   Autreare purified on a column of silica gel
8. 8
   Lavageeluting with a stepwise gradient of 3% to 15% methanol in dichloromethane
9. 9
   AutreThe product obtained
10. 10
    Lavageis washed with diisopropyl ether
11. 11
    Autrerecrystallized from isopropyl alcohol

Mode opératoire

To a suspension of 1.00 g (2.16 mmol) of ethyl 4-[2-(4-fluorophenyl)-6-(4-methylpiperazin-1-yl)imidazo[1,2-b]pyridazin-3-yl]-4H-pyridine-1-carboxylate in 35 mL of toluene is added a solution of 0.65 g (2.6 mmol) of ortho-chloranil in 6 mL of toluene. After reaction for 6 hours, 60 mL of 1N sodium hydroxide are added and the product is extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the solvent is evaporated off under reduced pressure. 1.2 g of solid are thus recovered, and are purified on a column of silica gel, eluting with a stepwise gradient of 3% to 15% methanol in dichloromethane. The product obtained is washed with diisopropyl ether and recrystallized from isopropyl alcohol to give 0.47 g of crystals after filtering off and drying under reduced pressure.

Source