Water → N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-oxoethyl]phthalimide

HRID 55991Notes

Reaction equation

HRID 55991 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][N:6]=1)=[O:4].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K].O>CN(C)C=O.[I-].[K+]>[Cl:11][C:10]1[C:5]([C:3](=[O:4])[CH2:2][N:20]2[C:19](=[O:21])[C:18]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]3[C:16]2=[O:26])=[N:6][CH:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24194345Phthalimide potassium saltHCID 860575962-Bromo-1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethanone

Product 1

HCID 66798033N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2-oxoethyl]phthalimideYield 34.9%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To 1.43 g of 2-bromo-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone in 10 ml of N,N-dimethylformamide, 0.68 g of potassium phthalimide and 0.01 g of potassium iodide were added, and the mixture was stirred at 85° C. for 1 hour. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, mixed with 10 ml of water and extracted with ethyl acetate (10 ml×3), the resulting organic layers were combined, washed with water and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography (preparative medium pressure chromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.) using ethyl acetate-hexane (with a gradient of from 5:95 to 46:60) as the eluent to obtain 0.47 g of the desired product as a pale yellow resinous substance.

Workup

  1. customAfter completion of the reaction
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate (10 ml×3)
  4. washwashed with water
  5. dry with materialdried over saturated aqueous sodium chloride
  6. customanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by preparative medium pressure liquid chromatography (preparative medium pressure chromatograph: YFLC-Wprep manufactured by Yamazen Science, Inc.)

Sources & evidence

ORD record
ord-89409cc34dd74d518b3c93d2c67dee4c
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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