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. Author manuscript; available in PMC: 2014 Dec 12.
Published in final edited form as: J Med Chem. 2013 Dec 2;56(23):9709–9724. doi: 10.1021/jm4014136

Scheme 2.

Scheme 2

Synthesis of 4- and additional 5-substituted analogues of 1a

aReagents and conditions: (a) bis(pinacolato)diboron, potassium acetate, PdCl2(dppf)2, DMF, 105 °C, 3 h; (b) 4-nitrophenyl boronic acid, Na2CO3, Pd(PPh3)4, DME, H2O, 70–80 °C, overnight; (c) boronic acids, Na2CO3, Pd(PPh3)4, DME, H2O, 70–80 °C, overnight; (d) CuI, KI, HMPA, 150 °C, 3 h;