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Regioselective Metalation and Functionalization of the Pyrazolo[1,5- a]pyridine Scaffold Using Mg- and Zn-TMP Bases
Moritz Balkenhohl1, Bruno Salgues1, Takahiro Hirai1
1Department of Chemistry , Ludwig-Maximilians-Universität München , Butenandtstr. 5-13, Haus F , 81377 Munich , Germany.
Abstract:
A regioselective functionalization of the pyrazolo[1,5- a]pyridine scaffold using Mg- and Zn-TMP bases (TMP = 2,2,6,6-tetramethylpiperidyl) in the presence or absence of BF3·OEt2 is described. Also, various functionalized pyrazolo[1,5- a]pyridines bearing an ester function (and an NHBoc or ethyl group) are magnesiated and functionalized, leading to polysubstituted heterocycles. Additionally, a sulfoxide directed ortho-metalation, followed by the transition-metal-free amination of a pyrazolo[1,5- a]pyridine sulfoxide, using a magnesium amide, is reported.
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