HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2392260Generated: October 30, 2026
Sodium Carbonate → Methyl 5-chloro-4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate
https://huagongshe.com/reaction/2392260
Participants
| Role | Name | HCID | Charge |
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| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Methyl 4-bromo-5-chlorothiophene-2-carboxylate | HCID 57826388 | — |
| Reactant | 1-ethyl-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 57826915 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 5-chloro-4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate | HCID 57826796 | 94% |
Reaction Steps
A mixture of methyl 4-bromo-5-chloro-2-thiophenecarboxylate (230 mg, 0.9 mmol), 1-ethyl-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (425 mg, 1.8 mmol), PdCl2(dppf) (65.9 mg, 0.09 mmol), and sodium carbonate (2N aq, 1.35 mL, 2.7 mmol) in THF (5 mL) was heated to 70° C. in a sealed tube. After 5 h, the reaction mixture was concentrated under vacuum and purified on silica (EtOAc/Hex, 40-60%) to afford the title compound (241 mg, 92%) as a light yellow solid: LC-MS (ES) m/z=285 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08273782B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-9d48b3181a064705b83508b7806f8de1 |
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| Source note | uspto-grants-2012_09 |
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