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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 2.

Scheme 2.

Synthesis of 3-benzoyl-5-(3,4-dimethoxyphenyl)-pyrrolo[2,3-b]pyridine 14

Reagents and conditions. a) hexamine, H2O, CH3COOH, 120°C ; b) NaH, TsCl, 0°C to rt ; c) 3,4-dimethoxyphenylboronic acid, Pd(PPh3)4, 2M K2CO3, toluene, EtOH, 105°C ; d) 3M PhMgBr, THF, rt; e) MnO2, THF, rt ; f) KOH, EtOH, 80°C.