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. Author manuscript; available in PMC: 2014 Mar 28.

Published in final edited form as: J Med Chem. 2012 Oct 26;55(22):10160–10176. doi: 10.1021/jm3012728

Scheme 1 — Methods Used in the Preparation of the Guanidinomethyl Biaryl Analogues 13–15^a

^aReagents and conditions: (a) 4-tert-Butylphenylboronic acid, Pd(PPh₃)₄, K₂CO₃, dioxane:H₂O (3:1), 82–84%, (b) NaBH₄, EtOH, 70–75%, (c) MsCl, Et₃N, DCM, 90% (for 7) and 70% (for 8), (d) NBS, CCl₄, light, 52%, (e) Diboc guanidine, DMF, K₂CO₃, quantitative, and (f) TFA:DCM (1:1), quantitative.