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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1023470Erstellt: 27. Oktober 2026

Dimethylformamide → 2-Chloro-4-[2-(4-fluoro-phenyl)-cyclohex-1-enyl]-pyridine

https://huagongshe.com/reaction/1023470

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDimethylformamideHCID 6228—
EduktSodium CarbonateHCID 10340—
Edukt2-Chloropyridine-4-boronic acid, pinacol esterHCID 5103408—
EduktTrifluoro-methanesulfonic acid 2-(4-fluoro-phenyl)-cyclohex-1-enyl esterHCID 86673616—
KatalysatorHCID 178419050HCID 178419050—
LösungsmittelWaterHCID 962—
Produkt2-Chloro-4-[2-(4-fluoro-phenyl)-cyclohex-1-enyl]-pyridineHCID 8667361758,3%

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

Trifluoro-methanesulfonic acid 2-(4-fluoro-phenyl)-cyclohex-1-enyl ester (200 mg, 0.62 mmol), 2-Chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (162 mg, 0.68 mmol), Bis(triphenylphosphine)Palladium (II) dichloride (43 mg, 0.062 mmol), Sodium Carbonate solution (2.0 M, 1.54 mL, 3.1 mmol) and DMF (3 mL) are mixed in a 5 mL microwave tube with a stir bar and the mixture is heated to 100° C. in microwave reactor for 30 min. The mixture is poured to water (10 mL) and extracted with EtOAc (10 mL×3). The organic extracts are washed with water (20 mL×1), brine (20 mL×1) and dried over anhydrous sodium sulfate. After concentration, the crude is purified by silica flash column chromatography using EtOAc in Heptane (gradient from 0% to 20%) to give 104 mg of the desired product.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08722709B2
Quelldatensatzuspto-grants-2014_05
ORD IDord-f918b3db77804691a76161ae6aea9624
Quellennotizuspto-grants-2014_05