Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Methylboronic Acid | HCID 139377 | — |
| Reactant | HCID 86692406 | HCID 86692406 | — |
| 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 86692502 | HCID 86692502 | 57.4% |
Reaction Steps
A suspension of 1-(3,5-dichloropyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (2.0 g) in Reference Example 22 (2), methylboronic acid (419 mg), 1,1′-bis(di-tert-butylphosphino)ferrocene (631 mg), palladium acetate (299 mg) and tripotassium phosphate (2.97 g) in 1,4-dioxane (35 ml) was stirred with reflux for 8 hours. After completion of the reaction, the mixture was allowed to cool, and 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-(5-chloro-3-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.07 g) as a yellow solid. MS (ESI) m/z: 230 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09150555B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-fea5e490c1104064ae1d890c6ea6a799 |
|---|
| Source note | uspto-grants-2015_10 |
|---|
