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. 2018 Mar 14;33(1):651–656. doi: 10.1080/14756366.2018.1444608

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© 2018 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.

This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Scheme 1. — Reagents and conditions: (a) (S)-1-Boc-3-hydroxypyrrolidine, anhydrous THF, NaH, rt, overnight, 70%; (b) 6-methoxy-3-pyridinylboronic acid, Na₂CO₃, PdCl₂ (dppf), DME/H₂O, reflux, 4 h, 65–81%; (c) (i)TFA, CH₂Cl₂, rt, 2 h, 23–91%; (ii) diverse acids, DMF, HATU, DIPEA, rt, 12 h, 23–91%; (d) (S)-1-Boc-3-aminopiperidine, DMF, DIPEA, 90 °C, 6 h, 90%; (e) 1-Boc-4-aminopiperidine, DMF, DIPEA, 90 °C, 6 h, 52%.