Water → Ethyl 1-(3-fluoro-2-pyridyl)-4-formyl-pyrazole-3-carboxylate

HRID 1517592Notes

Reaction equation

HRID 1517592 reaction equation
[CH:1]([C:3]1[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:5][NH:6][CH:7]=1)=[O:2].F[C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:20][C:19]1[C:14]([N:6]2[CH:7]=[C:3]([CH:1]=[O:2])[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:5]2)=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27831762,3-DifluoropyridineHCID 178470492HCID 178470492, compound

Product 1

HCID 58268637Ethyl 1-(3-fluoro-2-pyridyl)-4-formyl-pyrazole-3-carboxylateYield 28.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 4-formyl-1H-pyrazole-3-carboxylate (1.6 g, 9.52 mmol), 2,3-difluorpyridine (1.20 g) and potassium carbonate (1.97 g) in dimethylformamide (8 mL) is heated and stirred at 100° C. for 1.5 h. Then, the reaction mixture is stirred at room temperature overnight. Water is added, and the organic phase is extracted with ethyl acetate, decanted, dried over magnesium sulfate and solvent evaporated under reduced pressure. Crude is purified by normal phase Isco chromatography using ethyl acetate and hexane to give 711 mg of the title compound. MS (m/z): 264 (M+1).

Workup

  1. temperatureis heated
  2. stirringThen, the reaction mixture is stirred at room temperature overnight
  3. extractionthe organic phase is extracted with ethyl acetate
  4. customdecanted
  5. dry with materialdried over magnesium sulfate and solvent
  6. customevaporated under reduced pressure
  7. customCrude is purified by normal phase Isco chromatography

Sources & evidence

ORD record
ord-41d8fc2eb6cf4869b3e53e24b6bf0f66
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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