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. Author manuscript; available in PMC: 2014 Nov 1.
Published in final edited form as: Eur J Med Chem. 2013 Sep 29;69:881–907. doi: 10.1016/j.ejmech.2013.09.038

Scheme 5.

Scheme 5

Synthesis of 3-carboxamide-9-substituted-9H-carbazol derivatives 81-83 and 85.a

a Reagents and conditions: (a) methyl 4-bromobenzoate, 5 mol% Pd(OAc)2, 5 mol% rac-BINAP, K2CO3, toluene, μW at 160°C, 2h; (b) Pd(OAc)2, AcOH, reflux, 1 h; (c) n-pentyl bromide, Cs2CO3, DMF, μw at 140°C, 2 h; (d) KOH, EtOH/H2O, reflux, 16 h; (e) DIEA, DMAP, corresponding amine, EDAC·HCl, DCM, 16h; (f) tert-butyl N-(3-bromo-propyl)carbamate, NaOH, acetone, μW at 80°C, 1h.