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

HRID 982646Notes

Reaction equation

HRID 982646 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16](C(O)=O)=[C:15]3[N:10]([N:11]=[C:12]([O:20][CH3:21])[CH:13]=[CH:14]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C1C(=O)N([Br:29])C(=O)C1>CN(C=O)C.C(OCC)(=O)C>[Br:29][C:16]1[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[N:9][N:10]2[C:15]=1[CH:14]=[CH:13][C:12]([O:20][CH3:21])=[N:11]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 225623402-(3-fluoro-phenyl)-6-methoxy-pyrazolo[1,5-b]pyridazine-3-carboxylic Acid

Product 1

HCID 225623443-Bromo-2-(3-fluoro-phenyl)-6-methoxy-pyrazolo[1,5-b]pyridazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(3-fluoro-phenyl)-6-methoxy-pyrazolo[1,5-b]pyridazine-3-carboxylic acid (2.0 g) in anhydrous DMF (20 ml) was added n-bromosuccinimide (1.78 g) and the resulting solution stirred at ambient temperature for 3 hours. The reaction mixture was diluted with ethyl acetate (800 ml) and washed sequentially with water (10×100 ml) and sat. brine (25 ml), dried (Na2SO4), and concentrated to give the title compound as a buff solid (2.1 g, 93%).

Workup

  1. washwashed sequentially with water (10×100 ml) and sat. brine (25 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e69229a4406b4b9cb612ef9166b26c86
Source dataset
uspto-grants-2005_03
Patent number
US06861429B2

Reaction notes

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