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Suzuki cross‐coupling for the incorporation of labeled methyl groups onto aryl halides. A synthesis of [ 14 C]tosyl chloride and its use in the synthesis of [ 14 C]L‐738,167
Author(s) -
Braun Matthew P.,
Dean Dennis C.,
Melillo David G.
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199905)42:5<469::aid-jlcr207>3.0.co;2-t
Subject(s) - chemistry , tosyl , aryl , chloride , halide , regioselectivity , suzuki reaction , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , alkyl
A synthesis of [4‐methyl]‐ 14 C]tosyl chloride ( 2 ) has been developed which utilizes a Suzuki Cross‐Coupling reaction between 4‐iodophenylsulfonic acid and a labeled methyl borinate as the key step. This process avoids the poor regioselectivity typically attendant with aromatic sulfonation procedures. We now describe the use of this [ 14 C]tosyl chloride in the synthesis of the orally active fibrinogen receptor antagonist L‐738,167 ( 1 ). Copyright © 1999 John Wiley & Sons, Ltd.