Hydrochloric Acid → Ethyl 6-n-propylimidazo[1,2-b]pyridazin-2-ylcarboxylate

HRID 1160762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160762
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[N:7]=1.O1C[CH2:19][CH2:18][CH2:17]1.[Br-].C([Zn+])CC.Cl>Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:17]([C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[N:7]=1)[CH2:18][CH3:19]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 2779714ethyl 6-chloroimidazo[1,2-b]pyridazine-2-carboxylateHCID 178455869HCID 178455869, Verbindung

Produkt 1

HCID 23028126Ethyl 6-n-propylimidazo[1,2-b]pyridazin-2-ylcarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418745HCID 178418745, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Ethyl 6-chloroimidazo[1,2-b]pyridazin-2-ylcarboxylate (1.00 g, 4.43 mmol) and [1,3-bis(diphenylphosphino)propane]nickel (II) dichloride (0.24 g, 0.44 mmol) were added to tetrahydrofuran (8.0 ml) under a nitrogen stream, and a solution of n-propylzinc bromide in tetrahydrofuran (0.5 M, 13.3 ml, 6.65 mmol) was added dropwise thereto with stirring under ice-cooling. The mixture was stirred for 20 minutes under ice-cooling and for 0.5 hour at room temperature, and cold water (50.0 ml) was added to the reaction mixture which was then acidified with dilute hydrochloric acid. The reaction solution was extracted with ethyl acetate, and the extracts were combined and washed with dilute hydrochloric acid and a saturated saline solution. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrated residue was purified by silica gel column chromatography (acetone:hexane=1:3) to give the title compound as white crystals. The yield was 0.77 g (74.8%).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was stirred for 20 minutes under ice-
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. washwashed with dilute hydrochloric acid
  5. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrated residue was purified by silica gel column chromatography (acetone:hexane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-f9adea78aa284774b0818f5d8e5eab53
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816526B2

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