A novel practical synthesis of benzothiazoles via Pd-catalyzed thiol cross-coupling.
A convenient synthesis of substituted benzothiazoles from 2-bromoanilides has been accomplished. The various 2-bromoanilides were reacted with an alkyl thiolate in high yields using a palladium catalyst. The resulting sulfides were easily converted to the corresponding benzothiazoles via the simultaneous generation of thiols and condensation under basic or acidic conditions.
Process Research, PreClinical Development, Banyu Pharmaceutical Co., Ltd., 3 Okubo, Tsukuba, Ibaraki, 300-2611, Japan. takahiro_itoh@merck.com
Takahiro
T
Itoh
Toshiaki
T
Mase
D000813:Anilides / Q000737:chemistry*; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000813:Anilides; D052160:Benzothiazoles; D013438:Sulfhydryl Compounds; D010165:Palladium; D001966:Bromine