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Reagents and conditions: (a) 1-octyne, Pd(PPh3)4, CuI, Et3N, 50 °C, 12 h; (b) 3-ethynylpyridine, Pd(PPh3)4, CuI, Et3N, 80 °C, 3 days; (c) Pd/C, H2, EtOAc, 12 h, rt; (d) K2CO3, MeI, MeCN, overnight, rt.
