CC(C)(C)OC(=O)N1CCNCC1.Cc1cccc(Br)c1[N+](=O)[O-]>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>Cc1cccc(N2CCN(C(=O)OC(C)(C)C)CC2)c1[N+](=O)[O-]tert-butyl piperazine-1-carboxylate (172 mg, 0.93 mmol) and 1-bromo-3-methyl-2-nitrobenzene (0.124 mL, 0.93 mmol), were added to a stirred solution of diacetoxypalladium (20.78 mg, 0.09 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (107 mg, 0.19 mmol) and cesium carbonate (664 mg, 2.04 mmol) dissolved in dioxane (3 mL). The resulting solution was stirred at 80 °C under nitrogen overnight. The reaction mixture was filtered, dried under vaccum. The crude product was purified by flash chromatography on silica gel eluting with 5 to 15% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford tert-butyl 4-(3-methyl-2-nitrophenyl)piperazine-1-carboxylate (50.0 mg, 16.81 %) as a orange oil.
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