Zurück
HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 2100701Erstellt: 24. Oktober 2026

Cesium carbonate → N-[5-(4-methyl-3-pyridinyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

https://huagongshe.com/de/reaction/2100701

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktCesium carbonateHCID 10796—
EduktTriphenylphosphineHCID 11776—
Edukt3-Bromo-4-methylpyridineHCID 817630—
EduktN-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamideHCID 46899971—
Katalysatorpalladium(II) acetateHCID 167845—
Lösungsmittel1,4-DioxaneHCID 31275—
ProduktN-[5-(4-methyl-3-pyridinyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamideHCID 1163849952,3%

Reaktionsbedingungen

Temperatur160 °C

Reaktionsschritte

A mixture of Intermediate 3 (80 mg, 0.22 mmol), 3-bromo-4-methylpyridine (1 eq, 38 mg, 0.22 mmol) and cesium carbonate (1.5 eq, 108 mg, 0.33 mmol) in a 3:1 mixture of 1,4-dioxan:water (4 ml) was degassed with argon for 5 minutes. Palladium acetate (2 mg, 0.01 mmol), followed by triphenylphosphine (12 mg, 0.04 mmol) were then added and the whole mixture stirred at 160° C. for 20 mins in a microwave reactor. The reaction mixture was allowed to cool and partitioned between ethyl acetate and water. The organic layer was separated and evaporated under reduced pressure. The resulting product was purified on a 5 g Isolute™ Flash silica-gel column, eluting from 0-40% ethyl acetate in petroleum ether to give the title compound as a yellow oil (38 mg, 52%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07572819B2
Quelldatensatzuspto-grants-2009_08
ORD IDord-41c6bea85eaf422bbf2725e0b379016d
Quellennotizuspto-grants-2009_08