Reacción #45822

Ecuación de reacción

ammonia

1-Ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride

4-bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylic acid

hydroxybenzotriazole

→

compound

Rendimiento 99.1%

4-Bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxamide

Rendimiento 99.1%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction liquid
2. 2
   Temperaturawas cooled at 0° C.
3. 3
   workup.STIRRINGby further stirring at room temperature for 1 hour
4. 4
   OtroThe reaction liquid
5. 5
   Concentraciónwas concentrated under reduced pressure
6. 6
   workup.ADDITIONsaturated sodium bicarbonate water (200 ml) was added
7. 7
   Extracciónthe product was extracted with ethyl acetate (200 ml×2)
8. 8
   LavadoThe organic layer was washed with saturated brine (50 ml)
9. 9
   Secadodried over anhydrous magnesium sulfate
10. 10
    Concentraciónconcentrated under reduced pressure
11. 11
    Otrothe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3:2)

Procedimiento

1-Ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (1.61 g, 8.42 mmol) was added to an N,N-dimethylformamide (80 ml) solution of 4-bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylic acid (I-256) (2.62 g, 7.02 mmol) and hydroxybenzotriazole (1.14 g, 8.42 mmol), followed by stirring at room temperature for 1 hour. The reaction liquid was cooled at 0° C., then aqueous 28% ammonia (1.42 ml, 21.1 mmol) was put into it, followed by further stirring at room temperature for 1 hour. The reaction liquid was concentrated under reduced pressure, then saturated sodium bicarbonate water (200 ml) was added, the product was extracted with ethyl acetate (200 ml×2). The organic layer was washed with saturated brine (50 ml), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3:2) to obtain the entitled compound (2.59 g, 99%) as a yellow white solid.

Fuente