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Reagents and conditions: (a) CDI, THF, N2H4·H2O, 87%; (b) 4-fluorobenzoic acid, HATU, DIEA, Burgess reagent, THF, 82%; (c) 4M HCl in 1,4-dioxane, 93%; (d) 2-ethoxybenzene sulfonyl chloride, NEt3, DCM, 14%, (e) 4-fluorobenzonitrile, K2CO3, n-BuOH, 160 °C, 31%; (f) BnBr, K2CO3, DMF, 64%; (g) 4M HCl in 1,4-dioxane, 100%; (h) 2-ethoxybenzene sulfonyl chloride, DIEA, DCM, 54%; (i) 20% Pd(OH)2/C, MeOH, H-cube®, 25%.
