An Efficient Synthesis of 1-Methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine and Its N6-Substituted Analogues

Maxim A. Nechayev; Nikolay Yu. Gorobets; Sergiy M. Kovalenko; Andrey A. Tolmachev

doi:10.1055/s-0032-1318346

Synthesis, Table of Contents

Synthesis 2013; 45(7): 919-924
DOI: 10.1055/s-0032-1318346

paper

An Efficient Synthesis of 1-Methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine and Its N⁶-Substituted Analogues

Maxim A. Nechayev

^aNational University of Pharmacy, Pushkinska str. 53, Kharkiv 61002, Ukraine

^bEnamine Ltd., Alexandra Matrosova Str. 23, Kyiv 01103, Ukraine

,

Nikolay Yu. Gorobets*

^cLaboratory for Physicochemical Processes, SSI ‘Institute for Single Crystals’ of NAS of Ukraine, Lenina Ave 60, Kharkiv 61001, Ukraine Fax: +38(57)3409343 Email: gorobets@isc.kharkov.com

,

Sergiy M. Kovalenko

^aNational University of Pharmacy, Pushkinska str. 53, Kharkiv 61002, Ukraine

,

Andrey A. Tolmachev

^bEnamine Ltd., Alexandra Matrosova Str. 23, Kyiv 01103, Ukraine

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Abstract

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Abstract

An efficient synthesis of 1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine hydrochloride was achieved using simple sodium borohydride reduction of 6-benzyl-1-methyl-1H-pyrrolo[2,3-c]pyridin-6-ium bromide as the key step followed by its debenzylation with hydrogen over palladium on carbon on a multigram scale. Similarly, a series of N⁶-substituted 1-methyl-1H-pyrrolo[2,3-c]pyridin-6-ium halides were synthesized and reduced with sodium borohydride, showing this method to be applicable for the synthesis of different N⁶-substituted 1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridines.

Key words

heterocycles - cyclization - alkylation - reduction - hydrogenation

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References

References

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