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. 2019 Sep 23;24(19):3451. doi: 10.3390/molecules24193451

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© 2019 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

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Scheme 1 — Reagents and conditions: (a) KNO₃, H₂SO₄, RT, 1 h; (b) aqueous NaSMe (21 wt%), 150 °C, 18 h; (c) Na₂S₂O₄, THF/H₂O (3:2), 60 °C, 0.5 h; (d) 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid 13, MeSO₂Cl, pyridine, CH₃CN, RT, 13 h; (e) CH₃NH₂ (2.0 M in THF), THF, 60 °C, 5 h.