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. Author manuscript; available in PMC: 2022 Feb 5.
Published in final edited form as: Eur J Med Chem. 2020 Dec 3;211:113060. doi: 10.1016/j.ejmech.2020.113060

Scheme 1.

Scheme 1.

Synthesis of Bicyclic Heterocycle Analogsa

aReagents and Conditions: (a) 3-fluorobenzyl mercaptan, DIPEA, n-BuOH, 170 °C Microwave; (b) PhB(OH)2, Cu(OAc)2, pyridine, TEMPO, 3Å MS, air, DCE; (c) MeI, NaH, THF, 0 – 20 °C; (d) 10% aq. NaOH, Reflux; (e) 3-fluorbenzyl mercaptan, DIPEA, EtOH, 100 °C; (f) PhB(OH)2, Cu(OAc)2, pyridine, 3Å MS, air, DCM (g) O-(diphenylphosphinyl)hydroxylamine, LiHDMS, DMF, −10 – 20 °C; (h) PhNCS, NaH, 3-fluorobenzyl bromide, DMF, 0 − 20 °C.