Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Methylboronic Acid | HCID 139377 | — |
| Reactant | Ethyl 1-(5-bromopyridin-2-yl)-5-methylpyrazole-4-carboxylate | HCID 46739344 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Bis(ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane);iron(2+) | HCID 12976736 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86692492 | HCID 86692492 | 88.8% |
Reaction Steps
A suspension of 1-(5-bromopyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (4 g) in Reference Example 24 (2), methylboronic acid (1.54 g), 1,1′-bis(di-tert-butylphosphino)ferrocene (306 mg), palladium acetate (145 mg) and tripotassium phosphate (11 g) in 1,4-dioxane (30 ml) was stirred under reflux. After completion of the reaction, the mixture was allowed to cool, ice water and a saturated aqueous solution of ammonium chloride were added thereto, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give 5-methyl-1-(5-methylpyridin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (2.81 g) as a white solid. MS (ESI) m/z: 246 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09150555B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-0559587b64cf43fb81a0ee4ee9b23529 |
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| Source note | uspto-grants-2015_10 |
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