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Reagents and conditions: (a) NIS, DCM, r.t, 10 min, 66%; (b) 3-ethynylpyridine, Pd(PPh3)4, CuI, Et3N, dioxane, r.t., 1.5 h, 77%; (c) hydrazine hydrate, THF, 85 °C, 6 h, 77%; (d) CDI, DMF, 70 °C, 2 h, 92%; (e) 2-(1-(2,2-difluoroethyl)-1H-imidazol-4-yl)ethan-1-amine, Et3N, THF, r.t., 20 h, 58%.
