Methanol → 4-Chloro-2-(2,6-dichloro-4-methoxyphenyl)thiazolo[5,4-c]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-(2,6-dichloro-4-iodophenyl)thiazolo[5,4-c]pyridine (0.300 g, 0.68 mmol), racemic-2-di-t-butylphosphino-1,1′-binaphthyl (0.035 g, 0.0884 mmol), Pd(OAc)2 (0.015 g, 0.068 mmol), Cs2CO3 (0.332 g, 1.02 mmol) and MeOH (0.275 mL, 6.8 mmol) in toluene (3 mL) was degassed with a stream of argon and the reaction mixture was heated at 70° C. for 18 hours. After cooling to room temperature, additional racemic-2-di-t-butylphosphino-1,1′-binaphthyl (0.035 g) and Pd(OAc)2 (0.015 g) were added. The resulting mixture was then degassed with a stream of argon and heated at 70° C. for 18 hours. The crude reaction mixture was filtered through Celite® and the filtrate was combined with two crude reaction mixtures obtained following the same method using 4-chloro-2-(2,6-dichloro-4-iodophenyl)thiazolo[5,4-c]pyridine (0.46 mmol). The volatiles were removed under reduced pressure and the resultant residue was purified by column chromatography on silica gel eluting with 0-10% diethyl ether in petroleum ether to afford the title compound as an off-white solid (116 mg, 30% yield). LCMS (Method D): RT=4.34 min, m/z: 345 [M+H+].

Provenance & Evidence