Potassium Hydroxide → 3-Bromoimidazo[1,2-b]pyridazin-6-ol

HRID 870637Notes

Reaction equation

HRID 870637 reaction equation
[Br:1][C:2]1[N:6]2[N:7]=[C:8](Cl)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[OH-:12].[K+]>COCCOC.O>[Br:1][C:2]1[N:6]2[NH:7][C:8](=[O:12])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 606230023-Bromoimidazo[1,2-b]pyridazin-6-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 3-bromo-6-chloro-imidazo[1,2-b]pyridazine [13526-66-4] (425.7 mg, 1.8 mmol) in 1,2-dimethoxyethane (9 mL) was added a solution of potassium hydroxide [1310-58-3] (185.4 mg, 2.8 mmol) in water (9.0 mL) and the stirred resultant solution heated to reflux under N2 for 3d, cooled and partitioned between ethyl acetate and water. The water phase was evaporated to dryness, taken up in methanol, filtered, and evaporated to yield 3-bromo-imidazo[1,2-b]pyridazin-6-one as 340 mg of yellow solid. LRMS (ESI) m/z 214.0/216.0 [(M+H)]+, calc'd for C6H4BrN3O3: 214.02.

Workup

  1. temperatureheated
  2. temperaturecooled
  3. custompartitioned between ethyl acetate and water
  4. customThe water phase was evaporated to dryness
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-38352ec3f56646d5babd19053c442f65
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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