title: Selective Access to Heterocyclic Sulfonamides and Sulfonyl Fluorides via a Parallel Medicinal Chemistry Enabled Method.
abstract: A sulfur-functionalized aminoacrolein derivative is used for the efficient and selective synthesis of heterocyclic sulfonyl chlorides, sulfonyl fluorides, and sulfonamides. The development of a 3-step parallel medicinal chemistry (PMC) protocol for the synthesis of pyrazole-4-sulfonamides effectively demonstrates the utility of this reagent. This reactivity was expanded to provide rapid access to other heterocyclic sulfonyl fluorides, including pyrimidines and pyridines, whose corresponding sulfonyl chlorides lack suitable chemical stability.
authors.affiliation: Worldwide Medicinal Chemistry, Pfizer Worldwide Research and Development , Eastern Point Road, Groton, Connecticut 06340, United States.
authors.forename: Joseph W
authors.initials: JW
authors.lastname: Tucker
authors.affiliation: Worldwide Medicinal Chemistry, Pfizer Worldwide Research and Development , Eastern Point Road, Groton, Connecticut 06340, United States.
authors.forename: Lois
authors.initials: L
authors.lastname: Chenard
authors.affiliation: Worldwide Medicinal Chemistry, Pfizer Worldwide Research and Development , Eastern Point Road, Groton, Connecticut 06340, United States.
authors.forename: Joseph M
authors.initials: JM
authors.lastname: Young
mesh_terms: D002626:Chemistry, Pharmaceutical; D020650:Combinatorial Chemistry Techniques; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013441:Sulfinic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006571:Heterocyclic Compounds; D013441:Sulfinic Acids; D013449:Sulfonamides; C048899:sulfuryl fluoride
keywords: 3-step PMC protocol; heterocyclic sulfonamides; rapid access; sulfonyl fluorides