2-Propanone, 1-(acetyloxy)-3-chloro- → (6-Iodoimidazo[1,2-b]pyridazin-2-yl)methanol

HRID 1667854

Reaction equation

HRID 1667854 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([I:8])=[CH:6][CH:7]=1.C([O:12][CH2:13][C:14](=O)[CH2:15]Cl)(=O)C.C(=O)([O-])O.[Na+]>C(O)C>[I:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:15]=[C:14]([CH2:13][OH:12])[N:1]=2)[N:4]=1

Participants

5

Reactant 3

HCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 516892Sodium BicarbonateHCID 108678346-Iodopyridazin-3-amine

Product 1

HCID 57441048(6-Iodoimidazo[1,2-b]pyridazin-2-yl)methanolYield 20.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-amino-6-iodopyridazine (2.0 g, 9.0 mmol) in ethanol (40 mL) was added 3-chloro-2-oxopropyl acetate (2.73 g, 18.1 mmol), and the mixture was heated under reflux for 24 hr. After cooling the mixture to room temperature, saturated aqueous sodium hydrogencarbonate solution was added to the mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was collected by filtration and washed with ethyl acetate/hexane to give the title compound (498 mg, 20%) as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hr
  3. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under reduced pressure
  8. filtrationthe residue was collected by filtration
  9. washwashed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-1a9efd711d2c4f268edf9f049fa9c54e
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Linked notes

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