Suzuki Cross-Coupling for the incorporation of labeled methyl groups onto aryl halides. A synthesis of [14C]Tosyl chloride and its use in the synthesis of [14C]L-738,167

Article abstract of DOI:10.1002/(SICI)1099-1344(199905)42:5<469::AID-JLCR207>3.0.CO;2-T

A synthesis of [4-methyl-¹⁴C]tosyl chloride 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 [¹⁴C]tosyl chloride in the synthesis of the orally active fibrinogen receptor antagonist L-738,167.