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. Author manuscript; available in PMC: 2021 Mar 4.
Published in final edited form as: ACS Chem Neurosci. 2020 Feb 17;11(5):674–701. doi: 10.1021/acschemneuro.0c00003

Scheme 6. Synthesis of intermediate 28aa.

Scheme 6.

aReagents and conditions: (a) 8-Aminoquinoline, EDCI, HOBt, DCM, rt, 24h, (85%); (b) Methyl-3-bromo-5-iodobenzoate, 10 mol% Pd(OAc)2, 30 mol% PivOH, Ag2CO3, toluene, reflux, 3d, (40–48%); (c) NaOH, EtOH, reflux, 24h, (95%); (d) TBTA, DCM, rt, 24h, (74%).