N-Amination of Indoles on Pilot-Plant Scale via Simultaneous and Proportional Metering of Reagents

…, RG Hanna, GE Lee, Y Polverine, JT Klein

Index: Weiberth, Franz J.; Hanna, Reda G.; Lee, George E.; Polverine, Yvonne; Klein, Joseph T. Organic Process Research and Development, 2011 , vol. 15, # 3 p. 704 - 709

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Citation Number: 3

Abstract

The N-amination of indoles was a chemical transformation that was common in the synthesis of a series of target molecules that were in preclinical and clinical development in our company. Early batches of the N-aminoindoles were prepared using the method of Somei and Natsume(1) whereby indoles were treated with hydroxylamine-O-sulfonic acid (HOSA) in DMF in the presence of solid KOH. Several limitations were encountered upon scale up of this ...