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. Author manuscript; available in PMC: 2012 Jun 1.
Published in final edited form as: Bioorg Med Chem. 2011 Apr 24;19(11):3347–3356. doi: 10.1016/j.bmc.2011.04.042

Scheme 4.

Scheme 4

Reagents and conditions: (a) CuI, NaI, H2N(CH2)2NH2, 1,4-dioxane, 110 °C; (b) PdCl2(dppf), Ar-boronic acid or ester, K2CO3, Tol/EtOH/H2O/DMF, 90 °C; (c) PdCl2(PPh3)2, CuI, HC≡C-R, NEt3/DMF, 50–70 °C; (d) Boc2O, DMAP, DCM; (e) i) MsCl, NEt3, DCM, −20 °C, ii) morpholine or N-methylpiperazine, K2CO3, DMF, iii) TFA, DCM; (f) CuSO4, Na ascorbate, BnN3, DCM/EtOH/H2O, 20 °C; (g) ROH or RNH2, neat, Cs2CO3, 160–180 °C.