Reaktion #163174

Reaktionsgleichung

N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-benzene sulfonamide

4-nitropyrazole

trans-N,N′-dimethyl-cyclohexane-1,2-diamine

cesium carbonate

→

4-tert-butyl-N-[5-chloro-2-(4-nitro-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide

Lösungsmittel

water

Ethyl acetate

N,N-dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe layers were separated
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe crude reside was subsequently purified by flash column chromatography (0-100% ethyl acetate in hexanes)

Vorschrift

A solution of N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-benzene sulfonamide (534 mg, 1.32 mmol), 4-nitropyrazole (224 mg, 1.98 mmol), trans-N,N′-dimethyl-cyclohexane-1,2-diamine (42 μL, 0.264 mmol), copper iodide (51 mg, 0.264 mmol), and cesium carbonate (903 mg, 2.77 mmol) in 5 mL of N,N-dimethylacetamide was heated at 130° C. for 2 hours. Ethyl acetate and water were added and the layers were separated. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude reside was subsequently purified by flash column chromatography (0-100% ethyl acetate in hexanes) to afford 4-tert-butyl-N-[5-chloro-2-(4-nitro-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide as a white solid.

Quelle