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. Author manuscript; available in PMC: 2015 Mar 13.
Published in final edited form as: J Med Chem. 2013 Nov 6;57(5):1914–1931. doi: 10.1021/jm401329s

Scheme 1. Synthesis of 3,5,6,8-tetrasubstituted quinoline core.

Scheme 1

Reagents and conditions: (a) Ph2PON3, Et3N, EtOH, THF, reflux, 81%; (b) aq. KOH, EtOH, reflux, 96%; (c) NBS, DMF, quantitative; (d) Br2, 2-bromoprop-2-enal, AcOH, 100 °C, 45%; (e) 4-(methanesulfonamido)phenylboronic acid, Pd(PPh3)4, Na2CO3, MeOH, toluene, 120 °C, 57%.