Reacción #10398

Ecuación de reacción

2-bromo-3-chloro-4,5-difluorobenzoic acid

cyclopropyl amine

potassium acetate

triethylamine

→

title compound

Rendimiento 63.7%

3-Chloro-2-cyclopropylamino-4,5-difluorobenzoic acid

Rendimiento 63.7%

Disolventes

isopropyl alcohol

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthe reaction mixture is concentrated under vacuum
2. 2
   workup.DISSOLUTIONthe resulting residue is dissolved in ethyl acetate
3. 3
   LavadoThe organic layer is washed with 1.0 M hydrochloric acid, water, and brine
4. 4
   SecadoThe organic layer is dried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   ConcentraciónThe filtrate is concentrated under vacuum
7. 7
   Otropurified via flash column chromatography (5% isopropyl alcohol/1% formic acid/94% dichloromethane)

Procedimiento

In a sealed tube a mixture of 2-bromo-3-chloro-4,5-difluorobenzoic acid (Example 20, 7.96 g, 29.3 mmol), cyclopropyl amine (4.20 mL, 58.7 mmol), potassium acetate (5.77 g, 58.6 mmol), cupric acetate monohydrate (0.50 g, 2.5 mmol), and triethylamine (4.9 mL, 35.19 mmol) in isopropyl alcohol is stirred at 80° C. After 16 hours, the reaction mixture is concentrated under vacuum, and the resulting residue is dissolved in ethyl acetate. The organic layer is washed with 1.0 M hydrochloric acid, water, and brine. The organic layer is dried over MgSO4 and filtered. The filtrate is concentrated under vacuum and purified via flash column chromatography (5% isopropyl alcohol/1% formic acid/94% dichloromethane) to afford the title compound (4.62 g). MS CI: m/z 248 (MH+).

Fuente