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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 3. Synthetic Routes for Candidate Reverse-Azetidine B-SERDsa.

Scheme 3.

aReagents and conditions: (a) 11-boc-3-iodoazetidine, Cs2CO3, DMF, 140 °C, 50%. (b) CF3COOH, DCM, rt, 70%. (c) 1-Bromo-3-fluoropropane, NaH, 0–60 °C, 55%; or (1-methoxycyclopropoxy)trimethylsilane, AcOH, NaBH3CH, 80% (d) H2, Pd/C, rt, 70%. (e) 16a, 16b, 16d, 16f, 16g, Cs2CO3, DMF, 90 °C, 75–85%. (f) p-TsOH, MeOH, rt, 70–80%.