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. Author manuscript; available in PMC: 2019 Sep 13.
Published in final edited form as: J Med Chem. 2018 Aug 31;61(17):8029–8047. doi: 10.1021/acs.jmedchem.8b01133

Scheme 3. Synthesis of quinolines 21 and 23a.

Scheme 3.

aReagents: (a) aniline, NaNO2, HCl, AcOH, NaOAc, H2O, 30% yield; (b) SnCl2, HCl, reflux, 50% yield; (c) p-methoxybenzenesulfonyl chloride, pyridine, rt, 77% yield; (d) RBr, K2CO3, DMF, rt; (e) NaOH, MeOH, reflux, 67% yield over 2 steps. rt: room temperature