HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloroform → HCID 86692503, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Cyclopropylboronic acid | HCID 2760897 | — |
| Reactant | HCID 86692502 | HCID 86692502 | — |
| 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 86692503 | HCID 86692503 | 75.5% |
Reaction Steps
A suspension of 1-(5-chloro-3-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (600 mg), cyclopropylboronic acid (369 mg), 1,1′-bis(di-tert-butylphosphino)ferrocene (51 mg), palladium acetate (24 mg) and tripotassium phosphate (1.83 g) in 1,4-dioxane (5 ml) was stirred under reflux for 6 hours. After completion of the reaction, the mixture was allowed to cool, and chloroform was added, filtered through Celite, and then the filtrate was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give 1-(5-cyclopropyl-3-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (462 mg) as a yellow solid. MS (ESI) m/z: 286 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150555B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-b32ffbe27637406aa7cc861e9d9dec5e |
| Source note | uspto-grants-2015_10 |