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

HRID 407002Notes

Reaction equation

HRID 407002 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 679805887-Chloro-3-iodoimidazo[1,2-b]pyridazineYield 77.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-a375889df9424b4bb56a380b9e738cfd
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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