Potassium Fluoride → HCID 86692554, compound

HRID 1748601Notes

Reaction equation

HRID 1748601 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[C:16]([CH3:18])[C:15](I)=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2].C([Si](CC)(CC)[C:23]([F:26])([F:25])[F:24])C.[F-].[K+]>CN(C)C=O.CN1CCCC1=O.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([C:23]([F:26])([F:25])[F:24])=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 522689Potassium FluorideHCID 4204914Triethyl(trifluoromethyl)silaneHCID 86692553HCID 86692553, compound

Product 1

HCID 86692554HCID 86692554, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-(5-Iodo-4-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (395 mg), copper(I) iodide (1.13 g), triethyl(trifluoromethyl)silane (1.11 ml), and potassium fluoride (345 mg) were suspended in N,N-dimethylformamide (6.2 ml) and N-methylpyrrolidone (6.2 ml), and stirred at 70° C. for 9 hours. After completion of the reaction, the mixture was allowed to cool, extracted with ethyl acetate, the obtained organic layer was sequentially washed with 28% ammonia water, water, and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 5-methyl-1-[4-methyl-5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (271 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. washthe obtained organic layer was sequentially washed with 28% ammonia water, water, and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-297d1bb8220d49feac93e526296d6500
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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