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

  • Beilstein J Org Chem. 2012:8:2004-18. doi: 10.3762/bjoc.8.227.
Rajendra Surasani  1 ,  Dipak Kalita ,  A V Dhanunjaya Rao ,  K B Chandrasekhar
Affiliations
  • 1. Custom Pharmaceutical Services, Dr. Reddy's Laboratories Ltd., Miyapur, Hyderabad 50049, India ; Department of Chemistry, Institute of Science and Technology, JNTU University of Anantapur, Anantapur 515002, India.
PMID: 23209536 DOI: 10.3762/bjoc.8.227
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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