Robust Synthesis of Methyl 5-Chloro-4-fluoro-1H-indole-2-carboxylate: A Key Intermediate in the Preparation of an HIV NNRTI Candidate was written by Mayes, Benjamin A.;Chaudhuri, Narayan C.;Hencken, Christopher P.;Jeannot, Frederic;Latham, G. Mark;Mathieu, Steven;McGarry, F. Patrick;Stewart, Alistair J.;Wang, Jingyang;Moussa, Adel. And the article was included in Organic Process Research & Development in 2010.Recommanded Product: 4-Chloro-3-fluoro-2-iodoaniline This article mentions the following:
A synthetic preparation of Me 5-chloro-4-fluoro-1H-indole-2-carboxylate, a key intermediate towards phosphoindole inhibitors of HIV non-nucleoside reverse transcriptase, is described. The five-step synthesis involved Boc protection of the com. available 4-chloro-3-fluoroaniline and regioselective iodination at C-2. After facile Boc deprotection, cyclization of the resultant o-iodoaniline gave the corresponding 5-chloro-4-fluoroindole-2-carboxylic acid which was subsequently esterified to provide the target indole ester in 56% overall yield. Identification of 6-chloro-7-iodo-2(3H)-benzoxazolone as a significant side product in the iodination step led to the development of conditions which eliminated its formation in subsequent batches. Advantages of this alternative approach relative to existing methodologies include (1) potentially hazardous diazonium and azido species were not required, (2) regioisomeric products were not generated, and (3) chromatog. isolations were avoided, as all intermediates were easily crystallized As a result, the key indole ester was produced rapidly at 100-fold increased scale compared to previous reports with a 10-fold improvement in overall yield. In the experiment, the researchers used many compounds, for example, 4-Chloro-3-fluoro-2-iodoaniline (cas: 1018450-37-7Recommanded Product: 4-Chloro-3-fluoro-2-iodoaniline).
4-Chloro-3-fluoro-2-iodoaniline (cas: 1018450-37-7) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Recommanded Product: 4-Chloro-3-fluoro-2-iodoaniline
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com