2,4-Dioxo-4-phenyl-butyric acid ethyl ester → 1-(5-Methoxy-2-pyridyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester

HRID 1437259Notes

Reaction equation

HRID 1437259 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][N:4]=1)[NH2:2].[CH2:11]([O:13][C:14](=[O:26])[C:15](=O)[CH2:16][C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:12]>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:16]=[C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:1]([C:3]2[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][N:4]=2)[N:2]=1)=[O:26])[CH3:12]

Participants

4

Reactant 2

HCID 2265032,4-Dioxo-4-phenyl-butyric acid ethyl esterHCID 230902452-Hydrazinyl-5-methoxypyridine

Product 1

HCID 684408421-(5-Methoxy-2-pyridyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above-obtained 2-hydrazino-5-methoxypyridine (705 mg) and the 2,4-dioxo-4-phenylbutyric acid ethyl ester (1.12 g) prepared in Referential Example 123-1) in ethanol (25 mL) was refluxed under heat for 19 hours, and then cooled in air. The reaction solvent was removed under reduced pressure, and the residue was partitioned by use of ethyl acetate and saturated aqueous sodium hydrogencarbonate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and the residue was purified through silica gel chromatography (hexane-ethyl acetate), to thereby give 1-(5-methoxy-2-pyridyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester as an amorphous product (705 mg, 43%).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heat for 19 hours
  3. temperaturecooled in air
  4. customThe reaction solvent was removed under reduced pressure
  5. customthe residue was partitioned by use of ethyl acetate and saturated aqueous sodium hydrogencarbonate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate anhydrate
  8. filtrationfollowed by filtration
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified through silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a2b5440d4ba44d7499dee296ea7d76ee
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

Loading…