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

HRID 1067586Notes

Reaction equation

HRID 1067586 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 and dried with magnesium sulfate. After the dry product was 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 with magnesium sulfate
  5. concentrationAfter the dry product was concentrated under reduced pressure
  6. washeluted with hexane:ethyl acetate (5:1)
  7. customThe desired fraction was collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ffcf693d184b444e8fcd9a2c420dd100
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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