Reaktion #167891

Reaktionsgleichung

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

Ausbeute 56.0%

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

Ausbeute 56.0%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter reaction for 6 hours
2. 2
   Extraktionthe product is extracted with ethyl acetate
3. 3
   WaschenThe organic phase is washed with saturated aqueous sodium chloride solution
4. 4
   Trocknendried over sodium sulfate
5. 5
   Sonstigethe solvent is evaporated off under reduced pressure
6. 6
   Sonstige1.2 g of solid are thus recovered
7. 7
   Sonstigeare purified on a column of silica gel
8. 8
   Wascheneluting with a stepwise gradient of 3% to 15% methanol in dichloromethane
9. 9
   SonstigeThe product obtained
10. 10
    Waschenis washed with diisopropyl ether
11. 11
    Sonstigerecrystallized from isopropyl alcohol

Vorschrift

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.

Quelle