Reaktion #164277

Reaktionsgleichung

2-(5-Bromo-2-chloro-phenyl)-5-methoxy-benzoimidazole-1-carboxylic acid tert-butyl ester

cesium carbonate

BINAP

piperidin-4-yl-pyrrolidin-1-yl-methanone

→

title compound

Ausbeute 82.0%

2-{2-Chloro-5-[4-(pyrrolidine-1-carbonyl)-piperidin-1-yl]-phenyl}-5-methoxy-benzoimidazole-1-carboxylic acid tert-butyl ester

Ausbeute 82.0%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthe mixture was added to the first vial
2. 2
   Temperaturcooled to room temperature
3. 3
   workup.ADDITIONEtOAC (3 mL) was added
4. 4
   Filtrationthe mixture filtered off
5. 5
   SonstigeSolvent was removed
6. 6
   Sonstigethe crude recovered with EtOAc (3.5 mL)
7. 7
   Filtrationfiltered through a 2 g silica column (eluent EtOAc)

Vorschrift

Method F—Step a 2-(5-Bromo-2-chloro-phenyl)-5-methoxy-benzoimidazole-1-carboxylic acid tert-butyl ester (obtained as described in general method 4, step c) (0.10 g, 0.23 mmol), piperidin-4-yl-pyrrolidin-1-yl-methanone (0.05 g, 0.30 mmol) and cesium carbonate (0.37 g, 1.14 mmol) were placed into a dried vial and 3 cycles of vacuum/nitrogen were performed, then dry toluene (0.20 mL) was added. At the same time palladium acetate (0.01 g, 0.05 mmol), and BINAP (0.04 g, 0.07 mmol) were placed into a dried 4 mL vial under nitrogen and 3 cycles of vacuum/nitrogen were performed. Then dry toluene (0.40 mL) was added, at room temperature under nitrogen, and the mixture was added to the first vial. The reaction mixture was heated at 80° C. overnight, cooled to room temperature, EtOAC (3 mL) was added and the mixture filtered off. Solvent was removed and the crude recovered with EtOAc (3.5 mL) and filtered through a 2 g silica column (eluent EtOAc) to afford 0.10 g of the title compound (82%) without further purifications.

Quelle