Reaktion #1951083

Reaktionsgleichung

2-(4-amino-2-cyano-3-methylamino-phenyl)-2-methyl-3-oxo-butyric acid ethyl ester

4-fluoro-1-isothiocyanato-2-methyl-benzene

→

2-[4-cyano-2-(4-fluoro-2-methyl-phenylamino)-3-methyl-3H-benzoimidazol-5-yl]-2-methyl-3-oxo-butyric acid ethyl ester

Ausbeute 56.5%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITwas continued at room temperature for 24 h
2. 2
   FiltrationThe brown suspension was then filtered through a ½ inch thick pad of silica
3. 3
   Waschenwashed with THF
4. 4
   Einengenconcentrated to dryness
5. 5
   SonstigeThe resulting deep red solid was further purified by silica gel chromatography
6. 6
   Wascheneluting with ethyl acetate

Vorschrift

To a glass scintillation vial was added 2-(4-amino-2-cyano-3-methylamino-phenyl)-2-methyl-3-oxo-butyric acid ethyl ester (0.247 g, 0.854 mmol), followed by THF (5 mL) and a magnetic stir bar. To the resulting solution was added 4-fluoro-1-isothiocyanato-2-methyl-benzene (0.191 g, 1.14 mmol) and the solution was stirred at room temperature for 48 h. To the solution was then added mercuric oxide (0.222 g, 1.02 mmol), and stirring was continued at room temperature for 24 h. The brown suspension was then filtered through a ½ inch thick pad of silica, washed with THF, and concentrated to dryness. The resulting deep red solid was further purified by silica gel chromatography, eluting with ethyl acetate:hexane (0% -100%) to provide 2-[4-cyano-2-(4-fluoro-2-methyl-phenylamino)-3-methyl-3H-benzoimidazol-5-yl]-2-methyl-3-oxo-butyric acid ethyl ester (0.204 g, 56%) as a deep red solid. ESMS (m/z): (M+1)+ found, 423.

Quelle