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. Author manuscript; available in PMC: 2013 Jul 15.

Published in final edited form as: ACS Med Chem Lett. 2012 Apr 6;3(5):392–396. doi: 10.1021/ml3000287

Scheme 1 — Preparation of Boron-Based 4-OHT Bioisosteres

Reagents and conditions: (a) Propiophenone, TiCl₄, Zn, THF, reflux. (b) 2-(Dimethylamino)ethylchloride hydrochloride, Cs₂CO₃, DMF, 70–80 °C. (c) (CF₃SO₂)₂O, pyridine, CH₂Cl₂, 0 °C–rt. (d) , PdCl₂(dppf), KOAc, dioxane, reflux. (e) KHF₂, MeOH/H₂O, rt. (f) (CH₃)₃SiCl, CH₃CN, H₂O, rt.

graphic file with name nihms369849f6.jpg — Preparation of Boron-Based 4-OHT Bioisosteres

Reagents and conditions: (a) Propiophenone, TiCl₄, Zn, THF, reflux. (b) 2-(Dimethylamino)ethylchloride hydrochloride, Cs₂CO₃, DMF, 70–80 °C. (c) (CF₃SO₂)₂O, pyridine, CH₂Cl₂, 0 °C–rt. (d) , PdCl₂(dppf), KOAc, dioxane, reflux. (e) KHF₂, MeOH/H₂O, rt. (f) (CH₃)₃SiCl, CH₃CN, H₂O, rt.