Potassium Carbonate → HCID 178493143, compound

Participants

Reaction Steps

0.50 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-bromo-3H-imidazo[4,5-b]pyridine (example 6) and 0.41 g of 3,4-dimethoxyphenylboronic acid are dissolved in 25 ml of degassed dioxane. Then a solution of 0.415 g of potassium carbonate and 0.127 g of lithium chloride in 19 ml of degassed water and 0.173 g of tetrakis(triphenylphosphine)palladium(0) are added. The mixture is heated to reflux under N2 for 48 hours and, after cooling and addition of water, it is extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate, concentrated and the residue is chromatographed on a silica gel column (dichloromethane/methanol 30–26:1). Concentration of the chromatographically pure fractions and crystallisation from ethyl acetate gives 0.18 g of the title compound as a yellowish solid of m.p. 185–186° C. The mass spectrum shows the molecular peaks MH+ and 2MNa+ at 391.3 and 803.0 Da.

Provenance & Evidence