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Reagents and conditions: (a) (i) 5-fluoro-4-iodopyridin-3-amine, (PPh3)2PdCl2, CuI, NEt3, CH3CN, 70 °C; (ii) Pearlman’s catalyst, H2 balloon, EtOH, RT; (b) (2S,3S)-2-azido-3-(4-chlorophenyl)-3-(3,5-difluorophenyl)propanoic acid, POCl3, pyridine, 0 °C; (c) (i) PMe3, THF/H2O, 0 °C; (ii) HCl, dioxane/CH2Cl2, RT.
