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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 2359435Erstellt: 25. Oktober 2026

Dichloromethane → 2-(5-Methylpyridin-3-yl)quinoline-8-carboxylic acid

https://huagongshe.com/reaction/2359435

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDichloromethaneHCID 6344—
EduktPotassium Phosphate, TribasicHCID 62657—
Edukt5-Methylpyridine-3-boronic acidHCID 2762708—
Edukt2-Chloroquinoline-8-carboxylic acidHCID 19026201—
KatalysatorBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
LösungsmittelWaterHCID 962—
LösungsmittelDimethylformamideHCID 6228—
Produkt2-(5-Methylpyridin-3-yl)quinoline-8-carboxylic acidHCID 5815461172,1%

Reaktionsbedingungen

Temperatur125 °C

Reaktionsschritte

A mixture of 2-chloroquinoline-8-carboxylic acid (0.600 g, 2.8 mmol), 5-methylpyridin-3-ylboronic acid (0.410 g, 3.0 mmol), K3PO4 (1.1 g, 5.2 mmol), and Pd(dppf)Cl2.CH2Cl2 (0.10 g, 0.122 mmol) in DMF (3 mL) and water (1 mL) was microwave heated (125° C.×1 Hour). The mixture was filtered over celite and the celite cake was washed with ethyl acetate (30 mL). The filtrate was combined with 60 mL aqueous saturated NaHCO3 solution and the mixture was extracted with ethyl acetate (3×20 mL). The organic layers were combined, washed with brine, dried (MgSO4), and concentrated. The crude material was purified by flash chromatography (a gradient of 0 to 100% ethyl acetate in pentane) to obtain 2-(5-methylpyridin-3-yl)quinoline-8-carboxylic acid (0.535 g, 2.02 mmol).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08685970B2
Quelldatensatzuspto-grants-2014_04
ORD IDord-f9bb6a143c27405c83db57eab064cfba
Quellennotizuspto-grants-2014_04