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Synthesis of methyl(ethyl) pyrazolo[4,3-b]pyridine-6-carboxylates and their conversion to tert-butyl 4,5,6,7-tetrahydropyrazolo-[4,3-b]pyridine-6-carboxylates

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Chemistry of Heterocyclic Compounds Aims and scope

N-Boc-4-aminopyrazole-5-carbaldehydes react with methyl 3,3-dimethoxypropanoate or β-keto esters in acetic acid under reflux to form methyl(ethyl) pyrazolo[4,3-b]pyridine-6-carboxylates, which were converted to the corresponding tert-butyl carboxylates via intermediate carboxylic acids. Their subsequent hydrogenation on a 10% Pd/C catalyst at 100°C and 25 atm afforded tert-butyl 4,5,6,7-tetrahydropyrazolo[4,3-b]pyridine-6-carboxylates.

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Authors and Affiliations

  1. National University “Kyiv-Mohyla Academy”, 2 Hrygorija Skovorody St, Kyiv, 04655, Ukraine

    Georgiy G. Yakovenko

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St, Kyiv, 02660, Ukraine

    Georgiy G. Yakovenko, Eduard B. Rusanov & Mykhailo V. Vovk

  3. Lesya Ukrainka Eastern European National University, 13 Voli Ave, Lutsk, 43025, Ukraine

    Lesya N. Saliyeva

  4. Enamine Ltd., 78 Chervonotkatska St, Kyiv, 02094, Ukraine

    Il’ya S. Donchak

Authors
  1. Georgiy G. Yakovenko
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  2. Lesya N. Saliyeva
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  3. Eduard B. Rusanov
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  4. Il’ya S. Donchak
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  5. Mykhailo V. Vovk
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Correspondence to Georgiy G. Yakovenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(11), 1137–1145

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Yakovenko, G.G., Saliyeva, L.N., Rusanov, E.B. et al. Synthesis of methyl(ethyl) pyrazolo[4,3-b]pyridine-6-carboxylates and their conversion to tert-butyl 4,5,6,7-tetrahydropyrazolo-[4,3-b]pyridine-6-carboxylates. Chem Heterocycl Comp 57, 1137–1145 (2021). https://doi.org/10.1007/s10593-021-03032-z

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  • DOI: https://doi.org/10.1007/s10593-021-03032-z

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