HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 626575Generated: October 30, 2026
Cesium carbonate → HCID 90411230, compound
https://huagongshe.com/reaction/626575
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 | 2-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine | HCID 59322779 | — |
| Reactant | HCID 90409521 | HCID 90409521 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 90411230 | HCID 90411230 | 97.3% |
Reaction Steps
A mixture of Example A1 (0.500 g, 1.987 mmol), (R)-3-(dimethylamino)pyrrolidine-1-carboxamide hydrochloride (0.770 g, 3.97 mmol) and Cs2CO3 (1.295 g, 3.97 mmol) and Xantphos (0.230 g, 0.397 mmol) in dioxane (10 mL) was sparged with Ar, treated with Pd2(dba)3 (0.182 g, 0.199 mmol), sparged again with Ar and heated at 100° C. overnight. The mixture was cooled to RT, treated with THF, the solids removed via filtration, washed with THF and the filtrate concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford (R)-3-(dimethylamino)-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)pyrrolidine-1-carboxamide (720 mg, 97%). MS (ESI) m/z: 373.1 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09309224B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-21b0f79578c047809f78a1d92d4ef949 |
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| Source note | uspto-grants-2016_04 |
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