2-Bromo-1-(4-fluorophenyl)ethan-1-one → 6-Chloro-2-(4-fluorophenyl)-7,8-dimethylimidazo[1,2-b]pyridazine

HRID 1803877Notes

Reaction equation

HRID 1803877 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:10])=[C:6]([CH3:9])[C:7]=1[CH3:8].Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=O>C(O)C>[Cl:10][C:5]1[C:6]([CH3:9])=[C:7]([CH3:8])[C:2]2[N:3]([CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[N:1]=2)[N:4]=1

Participants

4

Reactant 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 69919433-Amino-6-chloro-4,5-dimethylpyridazine

Product 1

HCID 593677146-Chloro-2-(4-fluorophenyl)-7,8-dimethylimidazo[1,2-b]pyridazineYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 13 g (85 mmol) of 3-amino-6-chloro-4.5-dimethylpyridazine and 23 g (107 mmol) of 2-bromo-1-(4-fluorophenyl)ethanone in 130 mL of ethanol is refluxed for 16 hours. After cooling, the solvent is evaporated off under reduced pressure and the residue is taken up in chloroform. The organic phase is washed with diluted aqueous ammonia, dried over sodium sulfate and concentrated under reduced pressure to give a brown solid. This solid is triturated in acetone to give 19.2 g of a beige-colored powder.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is evaporated off under reduced pressure
  3. washThe organic phase is washed with diluted aqueous ammonia
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a brown solid
  7. customThis solid is triturated in acetone

Sources & evidence

ORD record
ord-6193de431c6e41e69d196123c3c78599
Source dataset
uspto-grants-2013_01
Patent number
US08354405B2

Reaction notes

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