Reaktion #169689

Reaktionsgleichung

4-(2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl)aniline

2-chloro-3-nitropyridine

→

N-[4-(2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl)phenyl]-3-nitropyridin-2-amine

Ausbeute 41.6%

Lösungsmittel

water

NMP

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter this time, the reaction mixture was cooled to ambient temperature
2. 2
   Extraktionextracted with ethyl acetate (2×75 mL)
3. 3
   WaschenThe combined organic layers were washed with water (50 mL)
4. 4
   Trocknenbrine (50 mL), dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenthe filtrate was concentrated under reduced pressure
7. 7
   SonstigeThe residue obtained
8. 8
   Sonstigewas purified by chromatography (silica, methylene chloride to 1:9 ethyl acetate/methylene chloride)

Vorschrift

A mixture of 4-(2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl)aniline (55 mg) and 2-chloro-3-nitropyridine (35 mg) in NMP (3 mL) was stirred at 140° C. overnight. After this time, the reaction mixture was cooled to ambient temperature, diluted with water (50 mL) and extracted with ethyl acetate (2×75 mL). The combined organic layers were washed with water (50 mL) then brine (50 mL), dried over sodium sulfate, and filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by chromatography (silica, methylene chloride to 1:9 ethyl acetate/methylene chloride) to afford N-[4-(2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl)phenyl]-3-nitropyridin-2-amine (34 mg) as a dark brown solid.

Quelle