Potassium Carbonate → HCID 178493138, compound

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Reaction Steps

0.166 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-bromo-3H-imidazo[4,5-b]pyridine (example 6) and 0.13 g of 4-aminophenylboronic acid are dissolved in 8 ml of degassed dioxane. Then a solution of 0.21 g of potassium carbonate and 0.042 g of lithium chloride in 6.5 ml of degassed water and 0.058 g of tetrakis(triphenylphosphine)palladium(0) are added. The mixture is heated to reflux under N2 for 24 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 30–15:1). Concentration of the chromatographically pure fractions gives 0.09 g of the title compound as a yellow solid of m.p. 117–119° C. The mass spectrum shows the molecular peak MH+ at 346.3 Da.

Provenance & Evidence