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. Author manuscript; available in PMC: 2014 Mar 12.
Published in final edited form as: Eur J Med Chem. 2012 Dec 20;60:395–409. doi: 10.1016/j.ejmech.2012.12.027

Scheme 4.

Scheme 4

Methods used in the preparation of 5-substituted 1-phenylnaphthalenes, 10–12. Reagents and conditions: (a) borane ester, Pd(OAc)2, KOAc, DMF, 80 °C; (b) 4-bromo-X-benzene [X = Cl or I], Pd(PPh3)4, K2CO, dioxane/H2O, 100 °C; (c) cyclopropylboronic acid, Pd(OAc)2, Pcy3, K3PO4, toluene/H2O, 100 °C; (d) NaBH4, EtOH, rt; (e) 1,3-bis(t-butoxycarbonyl)guanidine, PPh3, DIAD, toluene, 0 °C to rt; (f) TFA/CH2Cl2, 0 °C to rt.