Sodium Iodide → 1-(6-Chloroimidazo(1,2-b)pyridazin-3-yl)ethan-1-one

HRID 456044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456044
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]=[CH:9]N(C)C)=[CH:4][CH:3]=1.[Na+].[I-].Cl[CH2:16][C:17](=[O:19])[CH3:18]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]([C:17](=[O:19])[CH3:18])=[CH:9][N:8]=2)[N:7]=1

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 6802247[2-(6-Chloro-3-pyridazinyl)-2-azavinyl]dimethylamine

Produkt 1

HCID 132488051-(6-Chloroimidazo(1,2-b)pyridazin-3-yl)ethan-1-oneAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of N′-(6-chloro-pyridazin-3-yl)-N,N-dimethyl-formamidine (1.3 g, 7 mmol) in DMF (60 mL) was added NaI (1 g, 6.7 mmol) and chloroacetone (1 mL, 12.6 mmol). The mixture was heated at 80° C. overnight and then concentrated under reduced pressure. The residue was purified by column chromatography to afford 1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-ethanone (0.7 g) in 51% yield. 1H-NMR (400 MHz, CDCl3) δ ppm 8.42 (s, 1H), 8.05 (d, 1H), 7.31 (d, 1H), 2.77 (s, 3H).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-81f316cd6c6748b095ca0bfe48814ec7
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497368B2

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