86802-68-8Relevant articles and documents
Sequential C-S and S-N Coupling Approach to Sulfonamides
Chen, Kai,Chen, Wei,Han, Bing,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
supporting information, p. 1841 - 1845 (2020/03/04)
A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.
Development of a scalable process for CI-1034, an endothelin antagonist
Jacks, Thomas E.,Belmont, Daniel T.,Briggs, Christopher A.,Horne, Nicole M.,Kanter, Gerald D.,Karrick, Greg L.,Krikke, James J.,McCabe, Richard J.,Mustakis, Jason G.,Nanninga, Thomas N.,Risedorph, Guy S.,Seamans, Ronald E.,Skeean, Richard,Winkle, Derick D.,Zennie, Thomas M.
, p. 201 - 212 (2013/09/04)
A concise, convergent multikilogram synthesis of CI-1034 (1), a potent endothelin receptor antagonist, is described. A 15-step preparation from commercially available o-vanillin and benzenesulfonyl chloride employs a remarkably robust Suzuki coupling between a boronic acid and an aromatic sulfonate ester as the key synthetic step. A scalable route capable of producing multikilogram quantities of CI-1034 with no chromatographic steps is described in this contribution. Improvements to the process included using a 4-fluorobenzenesulfonate ester as a suitable substitute for the triflate group in the Suzuki reaction and the use of MgCl2 as a substitute for TiCl4 in a Dieckmann condensation to provide the benzothiazine dioxide core.
Preparation of Nonsymmetrical p-Benzoquinone Diimines for Evaluation as Protein Cleavage Reagents
Holmes, Thomas J.,Lawton, Richard G.
, p. 3146 - 3150 (2007/10/02)
In an effort to improve the yield, selectivity, and mildness of reaction conditions employed in protein cleavage with bisalkylating quinone diimines, a series of analogous reagents (1a-h) were prepared.These novel N1,N4 nonsymmetrica