HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 532424Generated: October 31, 2026
Cesium carbonate → 3-tert-Butoxycarbonylamino-5-(5-fluoropyridin-2-yl)thiophene-2-carboxylic acid methyl ester
https://huagongshe.com/reaction/532424
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reactant | Tri-tert-butylphosphine tetrafluoroborate | HCID 2734635 | — |
| Reactant | 2-Bromo-5-fluoropyridine | HCID 2783171 | — |
| Reactant | Methyl 5-bromo-3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate | HCID 57356848 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | 3-tert-Butoxycarbonylamino-5-(5-fluoropyridin-2-yl)thiophene-2-carboxylic acid methyl ester | HCID 68942928 | — |
Reaction Steps
Palladium(II) acetate (20 mg) was added to a solution of 5-bromo-3-tert-butoxycarbonylaminothiophene-2-carboxylic acid methyl ester (300 mg), 2-bromo-5-fluoropyridine (235.5 mg), bis(pinacolato)diboron (462.2 mg), tri-t-butylphosphonium tetrafluoroborate (77.64 mg) and cesium carbonate (871.9 mg) in dioxane/water (6 mL/1.5 mL). The solution was heated at 90° C. for 3 h. The reaction solution was then mixed with ethyl acetate and water. The aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The crude product was purified by preparative HPLC. The product with the molecular weight of 352.39 (C16H17FN2O4S) was obtained in this way; MS (ESI): 353 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08853208B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-d5be4c950e28456f942ec3c359c27ca3 |
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| Source note | uspto-grants-2014_10 |
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