Potassium Carbonate → HCID 178493153, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.12 g of 1-(4-bromo-benzene-sulfonyl)-4-methyl-piperazine, 0.978 g of bis-(pinacolato)-diboron, 0.06 g of 1,1′-bis-(diphenylphosphino)-ferrocene, 0.077 g of [1,1′-bis(diphenyl-phosphino)ferrocene]palladium-dichloride (complex with CH2Cl2), 1.03 g of potassium acetate in 40 ml of degassed dioxane are heated to 90° C. under N2 for 8 hours. To the resulting mixture 15 ml of degassed dioxane, 0.931 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-iodo-3H-imidazo[4,5-b]pyridine (starting material A1), 0.283 g of tetrakis(triphenylphosphine)-palladium(0) and a solution of 0.678 g of potassium carbonate and 0.208 g of lithium chloride in 15 ml of degassed water are added under N2. The mixture is heated to reflux under N2 for 16 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 15-10:1). Concentration of the chromatographically pure fractions and crystallization of the residue from ethylacetate gives 0.545 g of the title compound as a solid of m.p. 193-195° C. The mass spectrum shows the molecular peak MH+ at 493.4 Da.

Provenance & Evidence