Reacción #45543

Ecuación de reacción

4-bromo-2-(2,2-dimethylpropionylamino)-5-iodo-3-methoxy-6-methylbenzamide

trifluoromethanesulfonic acid anhydride

hydrochloric acid

→

N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction liquid
2. 2
   Extracciónfollowed by extraction with ethyl acetate (200 ml×2)
3. 3
   LavadoThe organic layer was washed successively with 1 N hydrochloric acid (200 ml×2), saturated sodium bicarbonate water (50 ml), saturated brine (50 ml)
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   Otrothe residue was purified twice by silica gel column chromatography (n-hexane:ethyl acetate=4:1)
7. 7
   Otroto obtain the entitled compound (1.86 g, quant.) as a pale yellow solid

Procedimiento

4-Dimethylaminopyridine (54.2 mg, 443 μmol) was added to a pyridine (40 ml) suspension of 4-bromo-2-(2,2-dimethylpropionylamino)-5-iodo-3-methoxy-6-methylbenzamide (I-5) (2.08 g, 4.43 mmol), followed by cooling at 0° C. To this, trifluoromethanesulfonic acid anhydride (2.25 ml, 13.3 mmol) was dropwise added, followed by stirring at room temperature for 2.5 hours, the reaction liquid was put into 1 N hydrochloric acid (200 ml), followed by extraction with ethyl acetate (200 ml×2). The organic layer was washed successively with 1 N hydrochloric acid (200 ml×2), saturated sodium bicarbonate water (50 ml), saturated brine (50 ml), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified twice by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the entitled compound (1.86 g, quant.) as a pale yellow solid.

Fuente