Potassium Carbonate → HCID 178493141, compound

Participants

Reaction Steps

0.76 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-iodo-3H-imidazo[4,5-b]pyridine (example 7) and 0.55 g of 4-hydroxyphenylboronic acid are dissolved in 30 ml of degassed dioxane. Then a solution of 0.55 g of potassium carbonate and 0.17 g of lithium chloride in 26 ml of degassed water and 0.23 g of tetrakis(triphenylphosphine)palladium(0) are added. The mixture is heated to reflux under N2 for 56 hours and, after cooling, addition of water and adjusting the pH to 7, 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 30–10:1). Concentration of the chromatographically pure fractions gives 0.30 g of the title compound as a solid of m.p. 206–208° C. The mass spectrum shows the molecular peaks MH+ and 2MNa+ at 347.3 and 714.9 Da.

Provenance & Evidence