Water → Ethyl 2-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-carboxylate

HRID 12428Notes

Reaction equation

HRID 12428 reaction equation
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:13]1([C:19]2[CH:20]=[N:21][NH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:13]1([C:19]2[CH:20]=[N:21][N:22]([C:2]3[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][CH:10]=[CH:11][N:12]=3)[CH:23]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1391064-PhenylpyrazoleHCID 2796614Ethyl chloronicotinate

Product 1

HCID 66719926Ethyl 2-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-carboxylateYield 79.8%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3.6 g of ethyl 2-chloronicotinate (19.4 mmol), 1.3 g of 4-phenylpyrazole (8.12 mmol), 4.4 g of K2CO3, 40 mg of 18-crown-6 and 30 mg of KI in 30 ml of N,N-dimethylformamide was stirred at 130° C. for 6 hours. For workup, H2O was added and, after extraction with ethyl acetate, the organic phase was washed with H2O and sat. NaCl solution. The crude product obtained after drying and concentration of the solution was purified by chromatography on silica gel (eluent: CH2Cl2/methanol 1-10%). In total, 1.9 g of an oil were obtained, which crystallized completely on standing in a refrigerator.

Workup

  1. extractionafter extraction with ethyl acetate
  2. washthe organic phase was washed with H2O and sat. NaCl solution
  3. customThe crude product obtained
  4. customafter drying
  5. customconcentration of the solution was purified by chromatography on silica gel (eluent: CH2Cl2/methanol 1-10%)

Sources & evidence

ORD record
ord-aeb25d55c5c44a93bfc760d7a5f85022
Source dataset
uspto-grants-2010_06
Patent number
US07728012B2

Reaction notes

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