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. Author manuscript; available in PMC: 2020 Dec 26.
Published in final edited form as: J Med Chem. 2019 Dec 10;62(24):11301–11323. doi: 10.1021/acs.jmedchem.9b01580

Scheme 2. Synthetic Routes for Candidate Piperidine, Azetidine, and Pyrrolidine B-SERDsa.

Scheme 2.

aReagents and conditions: (a) 1,2-dibromoethane, KOH, THF, reflux, 50%. (b) Azetidine hydrochloride, 3-methylazetidine hydrochloride, 20, 24, piperidine, NaH, THF, 0–60 °C, 55%, (c) p-TsOH, MeOH, rt, 60%. (d) 16a-i, Cs2CO3, DMF, 90 °C, 55–75%. (e) p-TsOH, MeOH, rt, 60–80%.