Potassium Carbonate → 3-(1-phenyl-1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridin-4(1H)-one

HRID 1747790Notes

Reaction equation

HRID 1747790 reaction equation
Cl[C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:3]=1.[C:19]1([N:25]2[C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=[N:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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>[C:19]1([N:25]2[C:29]([C:2]3[C:7](=[O:8])[CH:6]=[CH:5][N:4]([C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=4)[CH:3]=3)=[CH:28][CH:27]=[N:26]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 3

HCID 11430Potassium Carbonate2×HCID 580723671-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×HCID 895864343-chloro-1-[3-(trifluoromethyl)phenyl]pyridin-4(1H)-one

Product 1

HCID 680149263-(1-phenyl-1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridin-4(1H)-oneYield 3.5%

Reagents, catalysts & solvents 4

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-Chloro-1-[3-(trifluoromethyl)phenyl]pyridin-4(1H)-one (0.0247 g), 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.0365 g), potassium carbonate (0.0249 g) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.0032 g) were suspended in toluene (1 mL) and water (0.1 mL), and the suspension was heated under reflux for 22 hr under an argon atmosphere. To the reaction mixture were added 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.0365 g) and potassium carbonate (0.0249 g) at room temperature, and the mixture was heated under reflux for 1 day under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with aqueous sodium hydrogen carbonate solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by NH silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.2 mg).

Workup

  1. temperatureunder reflux for 22 hr under an argon atmosphere
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 day under an argon atmosphere
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by NH silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7b9042c79e374203b764097876ef2bb9
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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