N-bromobutanimide → 3-Bromo-6-difluoromethoxy-2-(3-fluoro-phenyl)-pyrazolo[1,5-b]pyridazine

HRID 1280414Notes

Reaction equation

HRID 1280414 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][CH:10]([F:28])[O:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)[CH:20]=2)[N:17]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:20]1[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)=[N:18][N:16]2[C:15]=1[CH:14]=[CH:13][C:12]([O:11][CH:10]([F:9])[F:28])=[N:17]2

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 225623316-Difluoromethoxy-2-(3-fluoro-phenyl)-pyrazolo[1,5-b]pyridazine

Product 1

HCID 225623333-Bromo-6-difluoromethoxy-2-(3-fluoro-phenyl)-pyrazolo[1,5-b]pyridazineYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-bromo succinimide (195 mg) was added to a solution of 6-difluoromethoxy-2-(3-fluoro-phenyl)-pyrazolo[1,5-b]pyridazine (251 mg) and sodium bicarbonate (185 mg) in anhydrous DMF (10 ml) and stirred for 18 h. The reaction mixture was diluted with ethyl acetate (300 ml) and washed with water (10×20 ml), brine (20 ml), dried (Na2SO4) and concentrated to give the title compound as a solid (293 mg, 91%).

Workup

  1. washwashed with water (10×20 ml), brine (20 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-45985f9b5cdb4445aca3687c08183b57
Source dataset
uspto-grants-2002_09
Patent number
US06451794B1

Reaction notes

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