Reaktion #641818

Reaktionsgleichung

(5-Bromo-pyridin-3-yl)-acetic acid ethyl ester

5-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde

potassium carbonate

→

[5-(4-fluoro-2-formyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeH2O, and the solution was purged with N2 for 20 minutes
2. 2
   Sonstigethe reaction was purged with N2 for another 25 minutes
3. 3
   Sonstigethe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Vorschrift

(5-Bromo-pyridin-3-yl)-acetic acid ethyl ester (1.91 g, 7.8 mmol), 5-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (50% pure; 2.94 g, 11.75 mmol), and potassium carbonate (3.25 g, 23.5 mmol) were combined in 2:1 DME:H2O, and the solution was purged with N2 for 20 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.45 g, 0.39 mmol) was added, and the reaction was purged with N2 for another 25 minutes and then stirred at 75° C. for 2 hours. The mixture was worked up with EtOAc and H2O, and the residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give [5-(4-fluoro-2-formyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester.

Quelle