N-Iodosuccinimide → 7-Chloro-3-iodoimidazo[1,2-b]pyridazine

HRID 407002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407002
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[N:14][N:13]2[CH:16]=[CH:17][N:18]=[C:12]2[CH:11]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:9][C:10]1[CH:15]=[N:14][N:13]2[C:16]([I:1])=[CH:17][N:18]=[C:12]2[CH:11]=1

Komponenten

5

Edukt 2

HCID 120273N-IodosuccinimideHCID 679802597-Chloroimidazo(1,2-b)pyridazine

Produkt 1

HCID 679805887-Chloro-3-iodoimidazo[1,2-b]pyridazineAusbeute 77,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-Iodosuccinimide (2.17 g, 9.65 mmol) was added to a solution of 7-chloroimidazo[1,2-b]pyridazine (0.988 g, 6.43 mmol) in N,N-dimethylformamide (25 mL). The reaction mixture was stirred at r.t. overnight. The mixture was diluted with ethyl acetate, washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (gradient: 0-50%) to afford the desired product (1.40 g, 77.9%). LCMS (M+H)+: m/z=279.9/281.9.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (gradient: 0-50%)

Quellen und Nachweise

ORD-Eintrag
ord-a375889df9424b4bb56a380b9e738cfd
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754114B2

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