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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 5.

Scheme 5.

Synthesis of 1-methyl-1H-pyrrolo[2,3-b]pyridine 26.

Reagents and conditions. a) NaH, MeI, THF, 0°C to rt ; b) HNO3, 0°C to rt ; c) 3,4-dimethoxyphenylboronic acid, Pd(PPh3)4, K2CO3, H2O, dioxane, 105°C ; d) H2, THF, rt ; e) nicotinoyl chloride, pyridine, THF, 1M NaOH, rt.