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Reagents and conditions: (a) CDI, DCM, 2-(cyclopropylmethoxy)ethanamine, 60 °C, 2 h, 45%; (b) 3-methoxy-5-((trimethylsilyl)ethynyl)pyridine, PdCl2(PPh3)2, CuI, TEA, TBAF, THF, 64 °C, 1 h, 41%; (c) ethynyl(trimethyl)silane, CuI, Pd(PPh3)2, TEA, THF, 65 °C, 1 h, 58%; (d) 2-fluoro-3-iodopyridine, CuI, Pd(PPh3)2, TEA, TBAF, THF, 65 °C,1 h.
