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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 3.

Scheme 3.

Synthesis of 3-phenyl-5-(3,4-dimethoxyphenyl)-pyrrolo[2,3-b]pyridine 19

Reagents and conditions. a) NIS, acetone, rt ; b) NaH, TsCl, THF, 0°C to rt ; c) PhB(OH)2, Pd(PPh3)4, K2CO3, toluene, EtOH, H2O, 90°C ; d) 3,4-dimethoxyphenylboronic acid, Pd(PPh3)4, K2CO3, toluene, EtOH, H2O, 105°C ; e) KOH, EtOH, 80°C.