Hydrochloric Acid → 2-Chloro-6-propylimidazo[1,2-b]pyridazine

HRID 969726

Reaktionsgleichung

Reaktionsgleichung von HRID 969726
[Br-].[CH2:2]([Zn+])[CH2:3][CH3:4].O1CCCC1.[Cl:11][C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][C:17](Cl)=[N:16][N:15]2[CH:21]=1.Cl>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:11][C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][C:17]([CH2:2][CH2:3][CH3:4])=[N:16][N:15]2[CH:21]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 144223582,6-Dichloroimidazo[1,2-b]pyridazineHCID 178455869HCID 178455869, Verbindung

Produkt 1

HCID 230280952-Chloro-6-propylimidazo[1,2-b]pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under a nitrogen stream, a solution of n-propylzinc bromide in tetrahydrofuran (0.5 M, 7.98 ml, 3.99 mmol) was diluted with toluene (5.0 ml), and 2,6-dichloroimidazo[1,2-b]pyridazine (0.50 g, 2.66 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.19 g, 0.27 mmol) were added thereto, and the reaction mixture was stirred for 2 hours at 80° C. After cooling, to the reaction mixture was added cold water (50 ml), acidified with dilute hydrochloric acid, extracted with ethyl acetate, and the extracts were washed with dilute hydrochloric acid, a saturated saline, an aqueous saturated sodium bicarbonate solution and a saturated saline in this order. The resulting organic layer was dried over anhydrous magnesium sulfate, filtrated and concentrated. The concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7) to give the title compound as white crystals. The yield was 0.31 g (59.6%).

Aufarbeitung

  1. additionwere added
  2. temperatureAfter cooling, to the reaction mixture
  3. extractionextracted with ethyl acetate
  4. washthe extracts were washed with dilute hydrochloric acid
  5. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customThe concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7)

Quellen und Nachweise

ORD-Eintrag
ord-f38b27477ba748549e40efb5c42ed7b5
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07307165B2

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