Development of a Synthesis of a 2,3-Disubstituted 4,7-Diazaindole Including Large-Scale Application of CH3Li/TiCl4-Mediated Methylation of an Enolizable Ketone
Organic Process Research & Development2015Vol. 19(7), pp. 806–811
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Franz J. Weiberth, Harpal S. Gill, George E. Lee, Duc P. Ngo, Frederick L. Shrimp, Xuemin Chen, Geoffrey A. D’Netto, Bryan R. Jackson, Ying Jiang, Narendra Kumar, F. E. ROBERTS, Evgeny Zlotnikov
Abstract
The chemical development of a 2,3-disubstituted 4,7-diazaindole is described. The requisite tertiary carbinol substrate was prepared employing in situ-generated CH3TiCl3 as a chemoselective and preferred reagent compared to CH3MgX for methyl addition to an enolizable ketone. The 4,7-diazaindole ring system was efficiently assembled via an intramolecular Chichibabin transformation. The optimized processes were performed on pilot-plant scale to provide kilogram quantities of the target molecule.
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