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. Author manuscript; available in PMC: 2022 Apr 22.
Published in final edited form as: J Med Chem. 2021 Mar 31;64(8):5099–5122. doi: 10.1021/acs.jmedchem.1c00164

Scheme 5. Synthesis of Triazole-Containing Derivatives 34–36 for the Aza-Scan of the Central Phenyl Ringa.

Scheme 5.

aReagents and Conditions: (a) SOCl2, MeOH, rt, 15 h, and 40%; (b) tert-butyl nitrite, azidotrimethylsilane, acetonitrile, rt, 1 h, and 37–65%; (c) 4-ethynyl-α,α,α-trifluorotoluene, CuSO4·5H2O, Na ascorbate, TBTA, tert-BuOH/H2O = 1:1, rt, 45 min, and 36–69%; (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, 85 °C, 4 h, and 35–91%; (e) KOH, MeOH/H2O = 2:1, 50 °C, 5 h, and 68–91%; and (f) TFA/THF = 2:1, rt, 0.5 h, and 60–65%.