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Reagents and conditions: (a) CH3OH, SOCl2, 0–23 °C (33%); (b) 1-ethynyl-4-(trifluoromethyl)benzene, CuI, PdCl2(PPh3)2, DMF, NEt3, 0–23 °C (81%); (c) (CF3SO2)2O, NEt3, CH2Cl2 (98%); (d) tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate, Pd(PPh3)4, K2CO3, DMF (67%); (e) LiOH (aqueous 0.5M), CH3OH reflux, then HCl (1 M aq), pH 1 (28%).
