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Reagents and conditions: (a) methyl 4′-aminobiphenyl-3-carboxylate, EtOH, 55 °C; (b) 4-bromobenzenethiol, BF3–OEt2, DCM, 0 °C to rt; (c) 3-methoxycarbonylphenyl boronic acid, Pd(PPh3)4, Cs2CO3, dioxane/water (5/1), 80 °C; (d) NaOMe/MeOH, 0 °C to rt; (e) phenylacetylene, CuSO4, Na ascorbate, EtOH/H2O (4/1), rt.
