3-Bromo-6-chloroimidazo(1,2-b)pyridazine → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanol

HRID 69227

Reaktionsgleichung

Reaktionsgleichung von HRID 69227
Br[C:2]1[N:6]2[N:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C([Mg]Br)C.[F:16][C:17]1[C:26]([CH:27]=[O:28])=[C:25]([F:29])[CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[N:22]2>C1COCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([CH:27]([C:26]3[C:17]([F:16])=[C:18]4[C:23](=[CH:24][C:25]=3[F:29])[N:22]=[CH:21][CH:20]=[CH:19]4)[OH:28])=[CH:3][N:4]=2)[N:7]=1

Komponenten

5

Edukt 3

HCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 579172825,7-Difluoroquinoline-6-carbaldehyde2×HCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 58147519(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3-Bromo-6-chloro-imidazo[1,2-b]pyridazine (4.40 g, 18.95 mmol) was dissolved THF (189 mL) and under nitrogen conditions, ethylmagnesium bromide solution (3 M, 6.32 mL) was added slowly. The RM was stirred at rt for 15 min then a solution of 5,7-difluoro-quinoline-6-carbaldehyde (Intermediate F, 3.66 g, 18.95 mmol) in THF was added. It was stirred at rt for 30 min. The reaction was quenched with 10% NH4Cl. The precipitate was filtered off and a first part of the title compound was obtained as a white solid. The filtrate was concentrated and was taken up with 10% NH4Cl. The precipitate was filtered off and was washed with EtOAc. A second part of the title compound was obtained as a brown solid (tR 0.8 min (conditions 2), MH+=347).

Aufarbeitung

  1. stirringIt was stirred at rt for 30 min
  2. customThe reaction was quenched with 10% NH4Cl
  3. filtrationThe precipitate was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-5fab9e5c4ddf43969e95217a7e0db204
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

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