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. Author manuscript; available in PMC: 2020 Jun 27.
Published in final edited form as: J Med Chem. 2019 Jun 12;62(12):5810–5831. doi: 10.1021/acs.jmedchem.9b00136

Scheme 1.

Scheme 1.

Synthesis of 3-substituted-5-aryl pyrrolo[2,3-b]pyridines 8a-p

Reagents and conditions. a) TMSA, Pd(PPh3)2Cl2, CuI, Et3N, THF, rt; b) KOtBu, NMP, 80°C; c) HNO3, 0°C to rt; d) Pd(PPh3)4, K2CO3, ArB(OH)2, H2O, dioxane, 105°C; e)H2, Pd/C, THF, rt; f)RCOCl, pyridine, THF, 1M NaOH, rt; g)RCOOH, BOP, Et3N, DMF, rt; h)PhSO2Cl, pyridine, rt.