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.