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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 33540Erstellt: 24. Oktober 2026

Cesium carbonate → Methyl 5-(3-chlorophenyl)nicotinate

https://huagongshe.com/de/reaction/33540

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktCesium carbonateHCID 10796—
EduktMethyl 5-bromopyridine-3-carboxylateHCID 699336—
Edukt2-(3-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 10037225—
KatalysatorHCID 178418397HCID 178418397—
Lösungsmittel1,2-DimethoxyethaneHCID 8071—
ProduktMethyl 5-(3-chlorophenyl)nicotinateHCID 2009985080,5%

Reaktionsschritte

104 mg (0.09 mmol)Pd(PPh3)4, 1.5 g (6.29 mmol) of 3-chlorophenylboronic acid pinacol ester 2.86 ml (8.58 mmol) and 3M cesium carbonate solution were added under argon at room temperature to a solution of 1.24 g (5.72 mmol) methyl-5-bromo-pyridine-3-carboxylate in 45 ml dimethoxyethane and the mixture was heated to reflux for 30 min. The reaction mixture was cooled to room temperature and evaporated. The residue was taken up with ethyl acetate, washed with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.14 g (72%) of 5-(3-Chloro-phenyl)-nicotinic acid methyl ester

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07429605B2
Quelldatensatzuspto-grants-2008_09
ORD IDord-48cf15a1bb314f92a712ee4b2305e794
Quellennotizuspto-grants-2008_09