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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

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktWaterHCID 962—
EduktCesium carbonateHCID 10796—
Edukttert-Butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylateHCID 57505869—
Edukt2-Bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridineHCID 86670544—
KatalysatorPalladium ChlorideHCID 24290—
KatalysatorFerrocene-1,1'-bis-(diphenylphosphine)HCID 635956—
LösungsmittelEthyl AcetateHCID 8857—
Lösungsmittel1,4-Dioxane--water (1/1)HCID 21886435—
Produkt1,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylateHCID 70665243—

Reaktionsbedingungen

Temperatur120 °C

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

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08993560B2
Quelldatensatzuspto-grants-2015_03
ORD IDord-806a556025984cc58feff664d5c4ebd7
Quellennotizuspto-grants-2015_03