Dimethylformamide → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone

HRID 40328

Reaktionsgleichung

Reaktionsgleichung von HRID 40328
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)=[O:4].[Cl:15][C:16]1[N:21]=[N:20][C:19](/[N:22]=[CH:23]/N(C)C)=[CH:18][CH:17]=1.CN(C=O)C>>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([C:2]([C:3]([C:5]3[CH:6]=[C:7]4[C:12](=[CH:13][CH:14]=3)[N:11]=[CH:10][CH:9]=[CH:8]4)=[O:4])=[CH:23][N:22]=2)[N:21]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 716996922-Bromo-1-(quinolin-6-yl)ethan-1-oneHCID 178484245HCID 178484245, Verbindung

Produkt 1

HCID 86630275(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanoneAusbeute 61,4 %

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A 100 mL RB flask was charged with 2-bromo-1-(quinolin-6-yl)ethanone (0.7011 g, 2.80 mmol), (E)-N′-(6-chloropyridazin-3-yl)-N,N-dimethylformamidine (0.518 g, 2.80 mmol), and DMF (10.0 ml, 129 mmol), equipped with a reflux condenser, then heated at 105° C. for 3 hours. The reaction mixture was concentrated, then triturated with MeOH to yield (6-chloroimidazo[1,2-b]pyridazin-3-yl)(quinolin-6-yl)methanone (0.530 g, 1.72 mmol, 61%) as a brown solid.

Aufarbeitung

  1. customequipped with a reflux condenser
  2. concentrationThe reaction mixture was concentrated
  3. customtriturated with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-8fc8e95f1cf14139b7f08442945ff403
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524900B2

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