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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 33527Erstellt: 24. Oktober 2026

Cesium carbonate → 5-(4-Trifluoromethoxy-phenyl)-nicotinic acid methyl ester

https://huagongshe.com/de/reaction/33527

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktCesium carbonateHCID 10796—
EduktMethyl 5-bromopyridine-3-carboxylateHCID 699336—
Edukt4-(Trifluoromethoxy)phenylboronic acidHCID 2734386—
KatalysatorHCID 178418397HCID 178418397—
LösungsmittelDimethylformamideHCID 6228—
Produkt5-(4-Trifluoromethoxy-phenyl)-nicotinic acid methyl esterHCID 5800259154,5%

Reaktionsbedingungen

Temperatur80 °C

Reaktionsschritte

81 mg (0.07 mmol)Pd(PPh3)4 was added under argon at room temperature to a solution of 1.0 g (4.63 mmol) methyl-5-bromo-pyridine-3-carboxylate in 23 ml N,N-dimethylformamide and the mixture was heated to 80° C. Then 2.26 g (6.94 mmol) cesium carbonate and 1.05 g (5.09 mmol) of 4-(trifluoromethoxy)phenyl boronic acid were added and the mixture was stirred at 80° C. over night. The reaction mixture was cooled to room temperature, filtered, and the filtrate evaporated. The residue was taken up with ethyl acetate, washed twice with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 0.75 g (49%) of 5-(4-Trifluoromethoxy-phenyl)-nicotinic acid methyl ester

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07429605B2
Quelldatensatzuspto-grants-2008_09
ORD IDord-35dac7309df84df983f033476176a726
Quellennotizuspto-grants-2008_09