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

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 su...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2021-11, Vol.57 (11), p.1137-1145
Main Authors: Yakovenko, Georgiy G., Saliyeva, Lesya N., Rusanov, Eduard B., Donchak, Il’ya S., Vovk, Mykhailo V.
Format: Article
Language:English
Subjects:
Acetic acid
Carboxylates
Carboxylic acids
Chemistry
Chemistry and Materials Science
Esters
Organic acids
Organic Chemistry
Pharmacy
Pyridine
Pyridines
Tiagabine
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-021-03032-z