Reaktion #87056

Reaktionsgleichung

N-(2-(5-chloro-1H-indol-3-yl)ethyl)oxazole-5-carboxamide

phenyl iodide

dichloromethane

triphenylphosphine

→

title compound

N-(2-(5-chloro-1H-indol-3-yl)ethyl)-2-phenyloxazole-5-carboxamide

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturafter cooling down the mixture
2. 2
   Sonstigewas partitioned between brine and dichloromethane
3. 3
   SonstigeThe two phases were separated
4. 4
   Extraktionthe aqueous layer was extracted with dichloromethane
5. 5
   SonstigeThe organic layer was dried
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

Vorschrift

Water (5 mL) was added to a pre-stirred mixture of N-(2-(5-chloro-1H-indol-3-yl)ethyl)oxazole-5-carboxamide intermediate 173 (0.107 g; 0.369 mmol), phenyl iodide (0.050 mL; 0.443 mmol), (1,1′-bis(diphenylphosphino) ferrocene)-dichloropalladium(II), complex with dichloromethane (0.015 g; 0.019 mmol), silver carbonate (0.204 g; 0.738 mmol) and triphenylphosphine (0.010 g; 0.037 mmol). The resulting mixture was stirred at 70° C. for 24 hours and after cooling down the mixture was partitioned between brine and dichloromethane. The two phases were separated and the aqueous layer was extracted with dichloromethane. The organic layer was dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.025 (19%) of the title compound as a yellow solid.

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