Potassium Carbonate → HCID 178493152, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.593 g of 1-(4-bromo-benzene-sulfonyl)-4-benzyl-piperazine, 0.42 g of bis-(pinacolato)-diboron, 0.025 g of 1,1′-bis-(diphenylphosphino)-ferrocene, 0.033 g of [1,1′-bis(diphenyl-phosphino)ferrocene]palladium-dichloride (complex with CH2Cl2), 0.442 g of potassium acetate in 8 ml of degassed dioxane are heated to 90° C. in a sealed tube under N2 for 16 hours. To the resulting mixture 4 ml of degassed dioxane, 0.371 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-iodo-3H-imidazo[4,5-b]pyridine (starting material A1), 0.113 g of tetrakis(triphenylphosphine)-palladium(0) and a solution of 0.27 g of potassium carbonate and 0.083 g of lithium chloride in 4 ml of degassed water are added under N2. The tube is sealed again, the mixture is heated to 110° under N2 for 17 hours and, after cooling, addition of water and adjusting the pH to 7, it is extracted three times with ethylacetate. The combined organic phases are dried over sodium sulfate, concentrated and the residue is chromatographed on a silica gel column (dichloromethane/methanol 22-20:1+1% NEt3). Concentration of the chromatographically pure fractions and crystallization of the residue from ethylacetate gives 0.128 g of the title compound as a brownish solid of m.p. 160-162° C. The mass spectrum shows the molecular peak MH+ at 569.4 Da.

Provenance & Evidence