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. Author manuscript; available in PMC: 2013 Mar 7.
Published in final edited form as: J Med Chem. 2012 Feb 16;55(5):2406–2415. doi: 10.1021/jm201690h

Scheme 1. Synthesis of nitro precursor 12.

Scheme 1

Reagents, conditions and yields: (i) HBr, AcOH, reflux, 9 h; 87%; (ii) I2, KI, NH4OH, rt, 48 h; 26%; (iii) a) 1-(3-butynyl)-2-(R)-methylpyrrolidine, Pd(OAc)2, (p-tol)3P, CuI, rt, 10 min; b) i-Pr2NH, MeCN, 60 °C,16 h; 28%.