Reacción #60249

Ecuación de reacción

6-(4-Bromo-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid methyl ester

N-chlorosuccinimide

→

pure desired product

Rendimiento 87.0%

6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid methyl ester

Rendimiento 87.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otro(5-6 days)
2. 2
   OtroThe reaction mixture is quenched by the addition of aqueous saturated sodium bisulfite solution
3. 3
   Otroto give a suspension
4. 4
   FiltraciónThe resulting solids are collected by filtration
5. 5
   Lavadowashed with water and diethyl ether
6. 6
   Otrodried under reduced pressure

Procedimiento

6-(4-Bromo-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid methyl ester 28a (6.38 g, 17.51 mmol) is dissolved in N,N-dimethylformamide (275 mL). N-chlorosuccinimide (2.36 g, 17.70 mmol) is added as a solid and the reaction mixture is stirred at room temperature under N2 until the reaction is complete (5-6 days). The reaction mixture is quenched by the addition of aqueous saturated sodium bisulfite solution to give a suspension. The resulting solids are collected by filtration, washed with water and diethyl ether and dried under reduced pressure to yield 6.07 g (87%) of the pure desired product as a beige solid. MS ESI (+) m/z 398, 400 (M+Br pattern) detected.

Fuente