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

ABSTRACT: 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.

SUBMITTER: Surasani R

PROVIDER: S-EPMC3511036 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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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 R Kalita Dipak D Rao A V Dhanunjaya AV Chandrasekhar K B KB

Beilstein journal of organic chemistry 20121119

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), Xantp ...[more]

PMID: 23209536

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