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. 2012:8:2004-18.
doi: 10.3762/bjoc.8.227. Epub 2012 Nov 19.

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

Rajendra Surasani  1 , Dipak Kalita, A V Dhanunjaya Rao, K B Chandrasekhar
Affiliations

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

Rajendra Surasani et al. Beilstein J Org Chem. 2012.

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.

Keywords: 7-azaindole; C–N bond; C–O bond; ligand; palladium catalyst.

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Figures

Figure 1
Figure 1
Representative drug candidates of amino-azaindole and phenyl-azaindole containing motifs.
Scheme 1
Scheme 1
Cross coupling of 4-bromo-7-azaindole with amides, amines, amino acid esters and phenols.
See this image and copyright information in PMC

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