HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1666478Generated: October 25, 2026
Potassium Carbonate → tert-Butyl 4-(1-(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethylidene)piperidine-1-carboxylate
https://huagongshe.com/reaction/1666478
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methylboronic Acid | HCID 139377 | — |
| Reactant | Tert-butyl 4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate | HCID 66876318 | — |
| Catalyst | Silver(II) oxide | HCID 92152 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | tert-Butyl 4-(1-(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethylidene)piperidine-1-carboxylate | HCID 66876390 | 79.3% |
Reaction Steps
To a solution of tert-butyl 4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate (Example 71, step 2) (420 mg, 0.818 mmol) in toluene (10 mL), under N2 was added methyl boronic acid (54 mg, 0.900 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (60 mg, 0.0818 mmol), potassium carbonate (226 mg, 1.64 mmol) and silver oxide (379 mg, 1.64 mmol). The reaction was heated to 85° C. overnight. The reaction was cooled down and filtered. The filtrate was washed with water and dried over MgSO4. Purification by silica gel column chromatography (0-5% MeOH/CH2Cl2) gave the title compound (291 mg, 79% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08044052B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-c14456802d7d425c9994544548be7e19 |
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| Source note | uspto-grants-2011_10 |
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