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. Author manuscript; available in PMC: 2016 Sep 1.
Published in final edited form as: Bioorg Med Chem. 2015 Jul 17;23(17):5693–5701. doi: 10.1016/j.bmc.2015.07.021

Scheme 1.

Scheme 1

Reagents and conditions: (a) 4-Pyridine boronic ester, Pd(PPh3)4, K2CO3, DME, H2O, 100 °C, 24 h (for 5a); (b) 2-fluoropyridine-4-boronic acid (for 5b) or 2-Chloropyridine-4-boronic acid (for 5c), Pd(OAc)2, P(o-tolyl)3, Na2CO3, DME, H2O, 80 °C, 5 h; (c) TFA, CH2Cl2, rt, 3 h; (d) Bis(pinacolato)diboron, KOAc, PdCl2(dppf), 1,4-dioxane, 110 °C, 18 h; (e) 3-amino-4-bromopyridine (for 8d), 4-bromo-2-methoxypyridine (for 8e), Pd(PPh3)4, K2CO3, 1,4-dioxane, H2O, 110 °C, overnight.