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Potassium Carbonate → 1-benzyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 1528077
Notes
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Reaction equation

HRID 1528077 reaction equation
[CH2:1]([N:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11](=[O:16])[C:10](Cl)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([N:24]2[C:28](B3OC(C)(C)C(C)(C)O3)=[CH:27][CH:26]=[N:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C(=O)([O-])O.[Na+].CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH2:1]([N:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11](=[O:16])[C:10]([C:28]2[N:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:25]=[CH:26][CH:27]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 580723671-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 866865601-benzyl-3-chloro-5-methoxypyridazin-4(1H)-one

Product 1

HCID 680149051-benzyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-oneYield 77.7%

Reagents, catalysts & solvents 4

HCID 11714597
Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)
Catalyst
HCID 962WaterSolvent2×
HCID 1140TolueneSolvent
HCID 516892Sodium BicarbonateSolvent

Procedure

1-Benzyl-3-chloro-5-methoxypyridazin-4(1H)-one (13.6 g), 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (22.0 g), potassium carbonate (51.0 g) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (1.92 g) were suspended in toluene (330 mL) and water (33.0 mL), and the suspension was heated under reflux under a nitrogen atmosphere for 24 hr. The reaction mixture was allowed to be cooled to room temperature, diluted with water and saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was recrystallized from ethyl acetate/hexane to give the title compound (15.1 g).

Workup

  1. temperatureunder reflux under a nitrogen atmosphere for 24 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b4b8d6f958dd411fa83dc2bc0ad69a40
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090586B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes