2-Bromopyridine → Ethyl 1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate

HRID 1712941Notes

Reaction equation

HRID 1712941 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O.[Cu](I)I>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1

Participants

8

Reactant 4

HCID 79732-BromopyridineHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 142179ethyl 1H-pyrazole-4-carboxylate

Product 1

HCID 15192741Ethyl 1-(pyridin-2-yl)-1H-pyrazole-4-carboxylateYield 68.2%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 1H-pyrazole-4-carboxylate (1.57 g, 11.2 mmol), 2-bromopyridine (5.5 mL, 57.7 mmol), copper iodide (0.463 g, 2.43 mmol), N,N′-dimethylethane-1,2-diamine (1.00 mL, 9.17 mmol) and potassium carbonate (3.32 g, 24.0 mmol) in toluene (50 mL) was allowed to stir at 110° C. overnight. The reaction mixture was allowed to cool to rt and then diluted with EtOAc. The organic mixture was filtered (filter paper) and the residue was purified by column chromatography to give ethyl 1-pyridin-2-yl-1H-pyrazole-4-carboxylate (1.66 g) as a white solid. LCMS: (FA) ES+ 218.4.

Workup

  1. temperatureto cool to rt
  2. filtrationThe organic mixture was filtered
  3. filtration(filter paper)
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5642a3cd296a4a58ae4eb618dc863c54
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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