반응 #10398

반응 방정식

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

cyclopropyl amine

potassium acetate

triethylamine

→

title compound

수율 63.7%

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

수율 63.7%

용매

isopropyl alcohol

반응 조건

후처리

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

실험 절차

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+).

출처