Methyl iodide → 6-Chloro-2-methoxyimidazo[1,2-b]pyridazine

HRID 1169122Notes

Reaction equation

HRID 1169122 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([OH:11])[N:10]=2)[N:7]=1.[H-].[Na+].[CH3:14]I>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([O:11][CH3:14])[N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 229893296-Chloroimidazo[1,2-b]pyridazin-2-ol

Product 1

HCID 229893386-Chloro-2-methoxyimidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.69 g of 6-chloro-2-hydroxyimidazo[1,2-b]pyridazine was suspended in 30 ml of N,N-dimethylformamide; 838 mg of a 60% sodium hydride dispersion in mineral oil was added little by little, followed by stirring at room temperature for 30 minutes. Under ice water cooling conditions, 1.2 ml of methyl iodide was added, followed by stirring at room temperature for 3 days. Ice water was added, followed by extraction with ethyl acetate; the extract was washed with saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane:ethyl acetate (5:1). The desired fraction was collected and concentrated to yield 1.05 g of the title compound.

Workup

  1. stirringby stirring at room temperature for 3 days
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe extract was washed with saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluted with hexane:ethyl acetate (5:1)
  7. customThe desired fraction was collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5653879cc60f4733beb3327a7a1338b5
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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