HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1961227Generated: November 2, 2026
Potassium Carbonate → methyl 4-(1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate
https://huagongshe.com/reaction/1961227
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Trimethylboroxine | HCID 574072 | — |
| Reactant | methyl 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate | HCID 57826395 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | methyl 4-(1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate | HCID 57826420 | 76.4% |
Reaction Steps
To a 350 mL sealed flask reactor was added methyl 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (3.45 g, 11.46 mmol) [prepared according to the procedure of Example 156], trimethylboroxine (2.7 ml, 19.40 mmol), K2CO3 (4.75 g, 34.4 mmol) and Pd(dppf)Cl2 (599 mg, 1.17 mmol) in N,N-Dimethylformamide (DMF) (57 mL). The reaction was heated at 110° C. for 1 hour, cooled to room temperature and partitioned between CHCl3/H2O. The organic layer was separated, dried with Na2SO4, adsorbed onto silica and purified via column chromatography (0-30% EtOAc/Hexane) affording the title compound (2.07 g, 8.76 mmol, 76%): LC-MS (ES) m/z=251 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08410158B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-33de0b6eb3c84f229370bb98ad9a481a |
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| Source note | uspto-grants-2013_04 |
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