Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, ami...

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Autores principales: Surasani, Rajendra, Kalita, Dipak, Rao, A V Dhanunjaya, Chandrasekhar, K B
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3511036/
https://www.ncbi.nlm.nih.gov/pubmed/23209536
http://dx.doi.org/10.3762/bjoc.8.227
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author Surasani, Rajendra
Kalita, Dipak
Rao, A V Dhanunjaya
Chandrasekhar, K B
author_facet Surasani, Rajendra
Kalita, Dipak
Rao, A V Dhanunjaya
Chandrasekhar, K B
author_sort Surasani, Rajendra
collection PubMed
description Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs(2)CO(3), dioxane and palladium catalyst precursors Pd(OAc)(2)/Pd(2)(dba)(3). The combination of Pd(OAc)(2), Xantphos, K(2)CO(3) and dioxane was found to be crucial for the C–O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives.
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spelling pubmed-35110362012-12-03 Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols Surasani, Rajendra Kalita, Dipak Rao, A V Dhanunjaya Chandrasekhar, K B Beilstein J Org Chem Full Research Paper Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs(2)CO(3), dioxane and palladium catalyst precursors Pd(OAc)(2)/Pd(2)(dba)(3). The combination of Pd(OAc)(2), Xantphos, K(2)CO(3) and dioxane was found to be crucial for the C–O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives. Beilstein-Institut 2012-11-19 /pmc/articles/PMC3511036/ /pubmed/23209536 http://dx.doi.org/10.3762/bjoc.8.227 Text en Copyright © 2012, Surasani et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Surasani, Rajendra
Kalita, Dipak
Rao, A V Dhanunjaya
Chandrasekhar, K B
Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols
title Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols
title_full Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols
title_fullStr Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols
title_full_unstemmed Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols
title_short Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols
title_sort palladium-catalyzed c–n and c–o bond formation of n-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3511036/
https://www.ncbi.nlm.nih.gov/pubmed/23209536
http://dx.doi.org/10.3762/bjoc.8.227
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AT raoavdhanunjaya palladiumcatalyzedcnandcobondformationofnsubstituted4bromo7azaindoleswithamidesaminesaminoacidestersandphenols
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