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.
Itoh
Takahiro
T
Process Research, PreClinical Development, Banyu Pharmaceutical Co., Ltd., 3 Okubo, Tsukuba, Ibaraki, 300-2611, Japan. takahiro_itoh@merck.com
Mase
Toshiaki
T
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