HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 879993Erstellt: 23. Oktober 2026
Water → 1,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate
https://huagongshe.com/de/reaction/879993
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | tert-Butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylate | HCID 57505869 | — |
| Edukt | 2-Bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridine | HCID 86670544 | — |
| Katalysator | Palladium Chloride | HCID 24290 | — |
| Katalysator | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Lösungsmittel | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Produkt | 1,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate | HCID 70665243 | — |
Reaktionsschritte
To a degassed mixture of 2-bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridine (2.83 g), 1,1-dimethylethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (4.54 g) and cesium carbonate (9.9 g) in dioxane:water (4:1, 40 ml) was added PdCl2.dppf (0.828 g). The reaction mixture was heated at 120° C. overnight. The reaction mixture was added to water and extraction was carried out with ethyl acetate. The organic layer was dried over sodium sulphate and the filtrate was concentrated in vacuo. The crude product was purified through silica, eluting with 0-40% ethyl acetate in hexane. Appropriate fractions were concentrated in vacuo to yield the title compound, 3.8 g (84%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08993560B2 |
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| Quelldatensatz | uspto-grants-2015_03 |
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| ORD ID | ord-806a556025984cc58feff664d5c4ebd7 |
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| Quellennotiz | uspto-grants-2015_03 |
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