Preparation of 3-substituted 4- or 6-azaindoles

ORGN 628

Juliang Zhu, Bristol-Myers Squibb Pharmaceutical Research Institute, Henry S. Wong, wongh@bms.com, Synthesis Group, Bristol-Myers Squibb Co, 5, Research Parkway, Wallingford, CT 06492, John F. Kadow, kadowj@bms.com, Discovery Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, CT 06492-7660, Nicholas A. Meanwell, Nicholas.Meanwell@bms.com, Department of Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, CT 06492, and Tao Wang, wangta@bms.com, Anti-infectious Department, Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, CT 06492.
3-substituted 4- and 6-azaindoles were prepared from ortho-methyl-nitro-pyridines in a one-pot operation. The procedure sequentially involved a) condensation of methyl-nitro-pyridine with N,N-dimethylformamide dimethyl acetal, b) alkylation or acylation of enamine intermediate, c) reduction of nitro group to amine and d) in situ cyclization of aniline nitrogen with enamine moiety.

 

Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005