Potassium Carbonate → HCID 21882692, compound

Participants

Reaction Steps

0.38 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-iodo-3H-imidazo[4,5-b]pyridine (example 7) and 0.37 g of 4-benzyloxy-3-fluorophenylboronic acid are dissolved in 16 ml of degassed dioxane. Then a solution of 0.276 g of potassium carbonate and 0.85 g of lithium chloride in 13 ml of degassed water and 0.115 g of tetrakis(triphenylphosphine)palladium(0) are added. The mixture is heated to reflux under N2 for 18 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 28:1). Concentration of the chromatographically pure fractions and crystallisation from ethyl acetate gives 0.21 g of the title compound as a yellowish solid of m.p. 168–170° C. The mass spectrum shows the molecular peak MH+ at 455.3 Da.

Provenance & Evidence