HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 967573Erstellt: 23. Oktober 2026
Cesium carbonate → tert-Butyl (3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-pyridin-4-ylazepan-3-ylcarbamate
https://huagongshe.com/de/reaction/967573
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | 4-Bromopyridine | HCID 14268 | — |
| Edukt | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Edukt | tert-Butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-yl]carbamate | HCID 23657400 | — |
| Katalysator | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Produkt | tert-Butyl (3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-pyridin-4-ylazepan-3-ylcarbamate | HCID 86595044 | 22,4% |
Reaktionsschritte
4-Bromopyridine (286 mg, 1.47 mmol) was added to a solution of tert-butyl (3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-ylcarbamate (200 mg, 0.588 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (20 mg, 0.035 mmol), tris(dibenzylideneacetone)dipalladium(0) (22 mg, 0.024 mmol), and cesium carbonate (268 mg, 0.823 mmol) in dioxane (6 mL) and the mixture was heated at 150° C. in a Personal Chemistry Smith Creator™ microwave reactor. After 30 min, an additional amount of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (20 mg, 0.035 mmol) and tris(dibenzylideneacetone)dipalladium(0) (22 mg, 0.024 mmol) were added. After 30 min, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water (2×), saturated brine, dried over magnesium sulfate, filtered and concentrated to give the title compound (55 mg). MS 418.2 (M+1).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US06953790B2 |
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| Quelldatensatz | uspto-grants-2005_10 |
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| ORD ID | ord-b78806487a0b406087c51a0c1b21d3f0 |
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| Quellennotiz | uspto-grants-2005_10 |
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