Process Development of 5-Fluoro-3-[3-[4-(5-methoxy-4-pyrimidinyl)-1- piperazinyl]propyl]-1H-indole Dihydrochloride
Organic Process Research & Development1997Vol. 1(4), pp. 300–310
Citations Over TimeTop 10% of 1997 papers
Neal G. Anderson, Thomas D. Ary, James L. Berg, Peter J. Bernot, Yeung Chan, Chien‐Kuang Chen, Merrill L. Davies, John D. DiMarco, Ronald D. Dennis, R.P. Deshpande, Dinh-Dai Hoang, Roberto Droghini, William Early, Jack Z. Gougoutas, John A. Grosso, John Harris, Oscar W. Haas, Paul A. Jass, Daniel H. Kim, Gus A. Kodersha, Atul S. Kotnis, Jean Lajeunesse, David A. Lust, Gary D. Madding, Sandeep Modi, Jerome L. Moniot, Andrew L. Nguyen, Venkatapuram A. Palaniswamy, Douglas W. Phillipson, James H. Simpson, D. Thoraval, David A. Thurston, Kai Tse, Robert E. Polomski, Donald L. Wedding, William J. Winter
Abstract
5-Fluoro-3-[3-[4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl]propyl]-1H-indole dihydrochloride (1) facilitates 5-HT neurotransmission and was an antidepressant drug candidate. The development of a safe, rugged process for the large-scale, chromatography-free preparation of this compound is described. The main areas of optimization included a Fischer indole synthesis, preparation and chlorination of a monohydroxypyrimidine, and coupling of the resultant fragments to prepare the drug substance.
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