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Sodium Carbonate → 6-Difluoromethoxy-2-(3-fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-pyrazolo[1,5-b]pyridazine

HRID 2307514
Notes
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Reaction equation

HRID 2307514 reaction equation
Br[C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[N:4][N:5]2[C:10]=1[CH:9]=[CH:8][C:7]([O:11][CH:12]([F:14])[F:13])=[N:6]2.C(=O)([O-])[O-].[Na+].[Na+].[CH3:28][S:29]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)(=[O:31])=[O:30]>CN(C=O)C.C(OCC)(=O)C>[F:13][CH:12]([F:14])[O:11][C:7]1[CH:8]=[CH:9][C:10]2[N:5]([N:4]=[C:3]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=3)[C:2]=2[C:35]2[CH:36]=[CH:37][C:32]([S:29]([CH3:28])(=[O:31])=[O:30])=[CH:33][CH:34]=2)[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 225623333-Bromo-6-difluoromethoxy-2-(3-fluoro-phenyl)-pyrazolo[1,5-b]pyridazine

Product 1

HCID 99325596-Difluoromethoxy-2-(3-fluoro-phenyl)-3-(4-methanesulfonyl-phenyl)-pyrazolo[1,5-b]pyridazineYield 38.1%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-bromo-6-difluoromethoxy-2-(3-fluoro-phenyl)-pyrazolo[1,5-b]pyridazine (286 mg) in DMF(20 ml) was added 2N aq sodium carbonate (10 ml). To this mixture was added 4-methanesulfonyl-phenylboronic acid (180 mg) and tetrakis triphenylphosphine palladium (0) (34 mg). The resulting mixture was stirred and heated to reflux for 18 hours. The cooled reaction mixture was diluted with ethyl acetate (300 ml) and the organic solution washed with water (10×30 ml) and brine (30 ml), dried (Na2SO4) and evaporated to give a gum which was purified by flash column chromatography with chloroform:ethyl acetate (50:1 to 5:1) as eluant. Combination of appropriate fractions and concentration gave the title compound as an off-white solid (132 mg, 37%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. customThe cooled reaction mixture
  4. washthe organic solution washed with water (10×30 ml) and brine (30 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give a gum which
  8. customwas purified by flash column chromatography with chloroform:ethyl acetate (50:1 to 5:1) as eluant
  9. concentrationCombination of appropriate fractions and concentration

Sources & evidence

ORD record
ord-ce572fecf7bd4ce19934fbc89e492de4
Source dataset
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06831097B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes