C1CNCCN1.N#Cc1ccc(Cl)cc1Br>C1COCCO1.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>N#Cc1ccc(Cl)cc1N1CCNCC1Tris(dibenzylideneacetone)dipalladium (0) (43.4 mg, 0.05 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (59.0 mg, 0.09 mmol) were added to a mixture of 2-bromo-4-chlorobenzonitrile (205 mg, 0.95 mmol), Cesium carbonate (463 mg, 1.42 mmol) and Piperazine (163 mg, 1.89 mmol) in dioxane (3 mL). Reaction vessel was placed in an oil bath set to 90 °C 2.45pm. LCMS o/n shows large product peak (222). Cooled, filtered through a silica plug, washing with EtOAc until filtrate is clear. Crude NMR is very messy, target deprioritized. Discarded.
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