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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 519332Erstellt: 25. Oktober 2026

Cesium carbonate → 2-Bromo-6-(7,7-difluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-fluorobenzyl Acetate

https://huagongshe.com/reaction/519332

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktCesium carbonateHCID 10796—
Edukt1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
Edukt2,6-Dibromo-4-fluorobenzyl acetateHCID 67016593—
EduktHCID 86683735HCID 86683735—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
Lösungsmittel1,4-DioxaneHCID 31275—
Produkt2-Bromo-6-(7,7-difluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-fluorobenzyl AcetateHCID 8668373662%

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

A 100-mL round-bottomed flask equipped with a reflux condenser was charged with 1,4-dioxane (40 mL), 113o (890 mg, 3.94 mmol), 2,6-dibromo-4-fluorobenzyl acetate 101c (3847 mg, 11.8 mmol), Pd2(dba)3 (180 mg, 0.197 mmol), XantPhos (227 mg, 0.394 mmol), and cesium carbonate (2.57 g, 7.88 mmol). After three cycles of vacuum/argon flush, the mixture was heated at 100° C. for 16 h. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 3:1 petroleum ether/ethyl acetate to afford 113p (1100 mg, 62%) as a white solid. MS-ESI: [M+H]+ 471.1.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09115152B2
Quelldatensatzuspto-grants-2015_08
ORD IDord-67e7368b209f4a1ba7c483220f7fd5d1
Quellennotizuspto-grants-2015_08