Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Cyclopropylboronic acid | HCID 2760897 | — |
| Reactant | HCID 86692500 | HCID 86692500 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86692499 | HCID 86692499 | 55.8% |
Reaction Steps
A suspension of 1-(6-chloropyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.6 g), cyclopropylboronic acid (776 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (124 mg), palladium acetate (67.6 mg) and tripotassium phosphate (3.83 g) in 1,4-dioxane (13 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 chloroform. 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 1-(6-cyclopropylpyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (911 mg) as a brown oil. MS (ESI) m/z: 272 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150555B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-461b45a23def491d9d77d7750eed2ab0 |
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| Source note | uspto-grants-2015_10 |
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