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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 2. Alternative synthesis of 3,5,6,8-tetrasubstituted quinoline core.

Scheme 2

Reagents and conditions: (a) (2-methoxy-3-pyridyl)boronic acid, Pd(PPh3)4, Na2CO3, MeOH, CH2Cl2, 115 °C, 54%; (b) Br2, 2-bromoprop-2-enal, AcOH, 100 °C, 27%.