HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 57946Generated: October 27, 2026
Cesium carbonate → tert-butyl N-[(3S)-1-(5-bromo-1-methyl-2-oxo-3-pyridyl)-3-piperidyl]carbamate
https://huagongshe.com/reaction/57946
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | tert-butyl N-[(3S)-piperidin-3-yl]carbamate | HCID 1514171 | — |
| Reactant | 3,5-Dibromo-1-methylpyridin-2(1H)-one | HCID 3614350 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | tert-butyl N-[(3S)-1-(5-bromo-1-methyl-2-oxo-3-pyridyl)-3-piperidyl]carbamate | HCID 86707131 | 59.4% |
Reaction Steps
A mixture of 3,5-dibromo-1-methyl-pyridin-2-one (2.000 mmol; 533.8 mg), tert-butyl N-[(3S)-3-piperidyl]carbamate (2.00 mmol; 401 mg), cesium carbonate (4.0 mmol; 1303 mg), Xantphos (0.3400 mmol; 202.8 mg), and tris(dibenzylideneacetone)dipalladium(0) (0.2000 mmol; 185.0 mg) in 1,4-Dioxane (10 mL) was purged with Argon, then sealed and stirred at 110° C. overnight. The mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated and the residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford tert-butyl N-[(3S)-1-(5-bromo-1-methyl-2-oxo-3-pyridyl)-3-piperidyl]carbamate as a yellow solid (458.6 mg, 59%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09434725B2 |
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| Source dataset | uspto-grants-2016_09 |
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| ORD ID | ord-02ec5b27673a4a4e92c7a0ba42499636 |
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| Source note | uspto-grants-2016_09 |
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