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

HRID 1747789Notes

Reaction equation

HRID 1747789 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[OH:8].F[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.O>[Cl:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67867alpha,alpha,alpha,3-TetrafluorotolueneHCID 178516476HCID 178516476, compound

Product 1

HCID 895864343-chloro-1-[3-(trifluoromethyl)phenyl]pyridin-4(1H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

3-Chloropyridin-4-ol (0.259 g), 1-fluoro-3-(trifluoromethyl)benzene (0.126 mL) and potassium carbonate (0.276 g) were suspended in N-methyl-2-pyrrolidone (1.2 mL), and the suspension was stirred at 150° C. for 2 hr. The reaction mixture was cooled to room temperature, diluted with water, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate) to give the title compound (28.1 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate)

Sources & evidence

ORD record
ord-0fdc4c89cceb4c0197b5ee492a2611ef
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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