N,N'-Dimethylethylenediamine → HCID 81504459, compound

HRID 1748474Notes

Reaction equation

HRID 1748474 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC.[CH2:15]([O:17][C:18]([C:20]1[CH:21]=[N:22][NH:23][CH:24]=1)=[O:19])[CH3:16].Cl[C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=1>O1CCOCC1.[Cu]I.O>[CH2:15]([O:17][C:18]([C:20]1[CH:21]=[N:22][N:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=2)[CH:24]=1)=[O:19])[CH3:16]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 142179ethyl 1H-pyrazole-4-carboxylate

Product 1

HCID 81504459HCID 81504459, compoundYield 12.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Copper (I) iodide (2.87 g), tripotassium phosphate (15.89 g) and N,N′-dimethylethylenediamine (4.8 ml) were added to a solution of 1H-pyrazole-4-carboxylic acid ethyl ester (2.1 g) and 2-chloro-5-(trifluoromethyl)pyridine (3.26 g) in 1,4-dioxane (150 ml), and the mixture was stirred at 120° C. for three hours. After completion of the reaction, the reaction solution was cooled to room temperature, water was added therein and extracted with ethyl acetate three times. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (544 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled to room temperature
  3. extractionextracted with ethyl acetate three times
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6f8963c409824fa594e83c9d1575ee9f
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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