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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 12983Erstellt: 23. Oktober 2026

Cesium carbonate → 2-{4'-[(3aR,6aR)-5-Methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]biphenyl-4-yl}-4,5-dihydropyridazin-3(2H)-one

https://huagongshe.com/de/reaction/12983

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktCesium carbonateHCID 10796—
Edukt2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 2734217—
Edukt2-(4'-bromobiphenyl-4-yl)-4,5-dihydropyridazin-3(2H)-oneHCID 68497342—
Edukt(3aR,6aR)-5-Methyloctahydropyrrolo[3,4-b]pyrrole dihydrochlorideHCID 68499270—
KatalysatorSilver(I) trifluoromethanesulfonateHCID 76223—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
LösungsmittelTolueneHCID 1140—
Produkt2-{4'-[(3aR,6aR)-5-Methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]biphenyl-4-yl}-4,5-dihydropyridazin-3(2H)-oneHCID 2474388215,6%

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

A small pressure tube equipped with a magnetic stir bar was charged with 100 mg of 2-(4′-bromobiphenyl-4-yl)-4,5-dihydropyridazin-3(2H)-one, 58 mg of (3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrole dihydrochloride, 350 mg of cesium carbonate, 15 mg of silver triflate, 4.2 mg of tris(dibenzylideneacetone)dipalladium, and 7.2 mg of 2-dicyclohexylphosphino-2′(N,N-dimethylamino)biphenyl and 2 ml of toluene. After sealing and purging with argon the tube was heated at 100° C. for 20 hours. Crude product was purified by flash chromatography (silica gel, gradient 2 to 10% methanol in dichloromethane), which yielded 17 mg of the title compound as a dark yellow oil. Mass spectroscopy gave (M+H)+ m/z 375.2, consistent with assigned structure.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07728031B2
Quelldatensatzuspto-grants-2010_06
ORD IDord-d13f1c111a6a4d28ac8fdd786615866a
Quellennotizuspto-grants-2010_06