Palladiumcatalyzed amination with benzophenone imine as a new, safe and practical alternative to nitration for the synthesis of 7amino2,1,3benzothiadiazoles

Palladiumcatalyzed amination of 7bromo4methyl2,1,3benzothiadiazole 7 with benzophenone imine as an ammonia equivalent is described as a new, safe and practical alternative to nitration for the synthesis of 7amino4methyl2,1,3benzothiadiazole 1 in high yield. This methodology was successfully scaledup in the pilot plant on 14.0kg scale of 7and was also utilized for the synthesis of 7amino4,6dimethyl2,1,3benzothiadiazole 12 by the amination of 7bromo4,6dimethyl2,1,3benzothiadiazole 10.