Acetic Acid → ethyl 1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)-1H-pyrazole-3-carboxylate

HRID 1437210Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH2:10][C:9](O)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:8]([C:18]2[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[N:7]=1)=[O:5])[CH3:2].C(O)(=O)C>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:8]([C:18]2[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 105 °C

Procedure

The above-obtained 5-hydroxy-1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)-4,5-dihydropyrazole-3-carboxylic acid ethyl ester (0.546 g) was dissolved in ethanol (11 mL). Acetic acid (0.456 mL) was added to the resultant mixture, followed by stirring at 105° C. for 4 hours. The mixture was cooled in air. Subsequently, the reaction mixture was partitioned by use of saturated aqueous solution of sodium hydrogencarbonate, water, and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give the title compound as a solid substance (0.516 g, 100%).

Workup

temperatureThe mixture was cooled in air
customSubsequently, the reaction mixture was partitioned by use of saturated aqueous solution of sodium hydrogencarbonate, water, and ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate anhydrate
filtrationfollowed by filtration
customThe solvent was evaporated under reduced pressure
customThe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-a90f3cd76840408284e802d271d5fe59
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622471B2

Reaction notes

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