Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | HCID 23143431 | HCID 23143431 | — |
| Catalyst | copper(I) bromide | HCID 24593 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 23090154 | HCID 23090154 | 71% |
Reaction Steps
In an argon atmosphere at room temperature, sodium methoxide (1.74 g) and copper(I) bromide (0.231 g) were added to the above-obtained 1-(5-bromo-2-pyridyl)-5-(2-pyridyl)pyrazole-3-carboxylic acid ethyl ester (3.00 g) in a mixture of methanol (30 mL) and toluene (30 mL). The resultant mixture was refluxed under heat for 47 hours, and then cooled in air. Water (50 mL) was added to the reaction mixture, followed by stirring at room temperature for 1.5 hours. The reaction mixture was partitioned by use of water, acetic acid (10 mL), and methanol-chloroform (1:10) solvent mixture. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, to thereby give the title compound as a solid (1.68 g, 71%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07622471B2 |
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| Source dataset | uspto-grants-2009_11 |
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| ORD ID | ord-86f68c64a1d24cfc90ea357eaafa1619 |
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| Source note | uspto-grants-2009_11 |
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