Reaktion #10398

Reaktionsgleichung

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

cyclopropyl amine

potassium acetate

triethylamine

→

title compound

Ausbeute 63.7%

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

Ausbeute 63.7%

Lösungsmittel

isopropyl alcohol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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+).

Quelle