5-(pyridin-4-yl)furan-2-carbaldehyde synthesis

Yield:342600-56-0 61%

Reaction Conditions:

with tetrakis-(triphenylphosphine)-palladium;potassium carbonate in ethanol;lithium hydroxide monohydrate at 70;Inert atmosphere;Sealed tube;Suzuki-Miyaura Coupling;

Steps:

7.9.1. General procedure for coupling of aldehyde intermediates

General procedure: A bromo-aldehyde (1 mmol), boronic acid (1.1e1.3 mmol), tetrakis(triphenylphosphine)palladium (0.05 mmol), potassium carbonate(3 mmol), water (3 ml), ethanol (4 ml) and toluene (4 ml)were added to a round-bottomed flask. The reaction mixture wasflushed with argon, sealed under septa and heated at 70 C overnight.After cooling to room temperature, water (50 ml) was added,and product was extracted with ethyl acetate (3 x 50 ml). Combinedextracts were washed with brine, dried with anhydrousmagnesium sulfate and evaporated under reduced pressure. Theproduct was purified by column chromatography on silica withchloroform or a mixture of methanol and chloroform (1:9).

References:

Staroń, Jakub;Kurczab, Rafa?;Warszycki, Dawid;Sata?a, Grzegorz;Krawczyk, Martyna;Bugno, Ryszard;Lenda, Tomasz;Popik, Piotr;Hogendorf, Adam S.;Hogendorf, Agata;Dubiel, Krzysztof;Mat?oka, Miko?aj;Moszczyński-P?tkowski, Rafa?;Pieczykolan, Jerzy;Wieczorek, Maciej;Zajdel, Pawe?;Bojarski, Andrzej J. [European Journal of Medicinal Chemistry,2020,vol. 185,art. no. 111857] Location in patent:supporting information