Reaktion #164273

Reaktionsgleichung

piperidine-4-carboxylic acid ethyl ester

2-(5-Bromo-2-chloro-phenyl)-imidazo[4,5-c]pyridine-3-carboxylic acid tert-butyl ester

2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

cesium carbonate

→

mixture

Ausbeute 126.7%

1-[4-Chloro-3-(3H-imidazo[4,5-c]pyridin-2-yl)-phenyl]-piperidine-4-carboxylic acid ethyl ester

Ausbeute 126.7%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewere placed into a dried schlenk
2. 2
   workup.WAITleft
3. 3
   Temperaturcooling to room temperature
4. 4
   Filtrationfiltered through sodium sulphate (Na2SO4)
5. 5
   SonstigeThe crude was purified by flash chromatography (eluent gradient: EtOAc 100% to EtOAc:MeOH/95:5)

Vorschrift

Method C—Step d 2-(5-Bromo-2-chloro-phenyl)-imidazo[4,5-c]pyridine-3-carboxylic acid tert-butyl ester (0.50 g, 1.23 mmol), tris(dibenzylideneacetone) dipalladium(0) (Pd2 dba3) (0.13 g, 0.18 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (Xphos) (0.17 g, 0.37 mmol) and cesium carbonate (1.20 g, 3.68 mmol) were placed into a dried schlenk and few cycles of vacuum/nitrogen were performed. Then dry dioxane (2.00 mL) and piperidine-4-carboxylic acid ethyl ester (0.38 mL, 2.45 mmol) were added, the reaction mixture was heated at 80° C. for 4 h, left cooling to room temperature and filtered through sodium sulphate (Na2SO4). The crude was purified by flash chromatography (eluent gradient: EtOAc 100% to EtOAc:MeOH/95:5), to obtain 0.60 g of a mixture of the title compound and the starting material deprotected (7:3). The mixture was used for the next step.

Quelle