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

HRID 515559Notes

Reaction equation

HRID 515559 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH3:9])[C:3]=1[CH3:10].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:1][C:2]1[C:3]([CH3:10])=[C:4]([CH3:9])[C:5]2[N:6]([CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[N:8]=2)[N:7]=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 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 13.0 g (82.5 mmol) of 6-chloro-4,5-dimethylpyridazin-3-ylamine and 23.2 g (107 mmol) of 2-bromo-1-(4-fluorophenyl)ethanone in 130 ml of ethanol is refluxed for 16 hours. The solvent is evaporated off under reduced pressure, and the residue is taken up with chloroform and washed with a dilute solution of aqueous ammonia. The organic phase is dried over sodium sulfate and then concentrated under reduced pressure. The brown solid obtained is triturated in acetone, to give 19.2 g of a beige powder after filtration and drying.

Workup

  1. temperatureis refluxed for 16 hours
  2. customThe solvent is evaporated off under reduced pressure
  3. washwashed with a dilute solution of aqueous ammonia
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe brown solid obtained
  7. customis triturated in acetone

Sources & evidence

ORD record
ord-1f0ba5a8f7c54829af5ed8b1a9ff4443
Source dataset
uspto-grants-2015_08
Patent number
US09108971B2

Reaction notes

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