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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 750165Erstellt: 24. Oktober 2026

Toluene → 2-benzyl-6-butyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

https://huagongshe.com/de/reaction/750165

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTolueneHCID 1140—
EduktPotassium CarbonateHCID 11430—
EduktButylboronic AcidHCID 20479—
Edukt2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterHCID 44451690—
KatalysatorHCID 178418397HCID 178418397—
LösungsmittelWaterHCID 962—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt2-benzyl-6-butyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterHCID 4445185073,7%

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

A mixture of 2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (300 mg), n-butylboronic acid (340 mg), tetrakis(triphenylphosphine)palladium(0) (80 mg), potassium carbonate (280 mg), toluene (6 ml) and THF (3 ml) was stirred at 100° C. under a nitrogen atmosphere for 12 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine. The solvent was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1) and crystallized from hexane to give the title compound (210 mg).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07402595B2
Quelldatensatzuspto-grants-2008_07
ORD IDord-aabba87175394c2c8a5369dc6e20589b
Quellennotizuspto-grants-2008_07