Реакция #10398

Уравнение реакции

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

cyclopropyl amine

potassium acetate

triethylamine

→

title compound

Выход 63.7%

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

Выход 63.7%

Растворители

isopropyl alcohol

Условия реакции

Обработка

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

Методика

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+).

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