C1CNCCN1.NC(=O)c1cc2c(Br)cccc2o1>C1CCOC1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>NC(=O)c1cc2c(N3CCNCC3)cccc2o1The crude product from EN03731-54-001, 4-bromobenzofuran-2-carboxamide (0.600 g, 2.5 mmol), was dissolved in THF (18 mL) and water (18.00 mL). To this mixture were added piperazine (1.077 g, 12.50 mmol), Cesium carbonate (1.629 g, 5.00 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.114 g, 0.13 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.156 g, 0.25 mmol) and the reaction was heated at 70 °C over night. 2010-04-13 No product was detected. The reaction mixture was filtered and solvents were removed in vacuo. The residue was partitioned between methylene chloride and water. The organic layer was washed with 1M HCl(aq), dired with sodium sulfate, filtered, concentrated and purified by flash chromatography(Isolute Si 70g, methylene chloride: methanol; 97:3). No product could be detected/isolated.
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