تفاعل #10398

معادلة التفاعل

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

cyclopropyl amine

potassium acetate

triethylamine

→

title compound

المردود 63.7%

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

المردود 63.7%

المذيبات

isopropyl alcohol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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+).

المصدر