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Reagents and conditions: (a) 4-iodotoluidine, trans-1,2-cyclohexanediamine, K3PO4, CuI, toluene, 110 °C, 1 d, 48% yield; (b) m-phenylenediamine, DIEA, NMP, 150 °C, 4 d, quant. yield; (c) 4-nitrobenzoyl chloride, pyridine, rt, overnight; (d) SnCl2·2H2O, EtOAc/MeOH, 80 °C, 1 d, 40% yield over 2 steps; (e) 4-bromocrotonyl chloride, DIEA, ACN, 0 °C; (f) dimethylamine (2.0 M in THF), rt, 1 h, 4% yield over 2 steps.
