1-Methylpiperazine → Ethyl 4-[(2,4-difluorophenyl)amino]-6-(4-methylpiperazin-1-yl)quinoline-3-carboxylate

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To a solution of ethyl 6-bromo-4-(2,4-difluorophenylamino)quinoline-3-carboxylate hydrochloride (505 mg, 1.14 mmol) and 1-methylpiperazine (0.189 mL, 1.71 mmol) in dioxane (10 mL) was added cesium carbonate (1113 mg, 3.41 mmol), tris(dibenzylideneacetone)dipalladium(0) (52.1 mg, 0.06 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (70.9 mg, 0.11 mmol). Reaction vessel in oil bath set to 100 °C. 3pm o/n - 20 hours, LCMS shows mostly SM (408), trace of product (427). Heating stopped after 24 hours. 8/6/08 - Additional portions of Pd cat, BINAP and Me piperazine added, and reaction returned to oil bath at 105C. o/n - Reaction more advanced, but still mostly SM. From past experience, Buchwald coupling may be more successful if SM is purified on silica column first. Discarded

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