Reacción #155315

Ecuación de reacción

5-bromo-6-propoxyindan

benzophenone imine

9,9-dimethyl-4,5-bis (diphenylphosphino)xanthene

cesium carbonate

ammonium chloride

→

6-propoxy-indan-5-ylamine

Rendimiento 17.0%

Disolventes

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   Extracciónfollowed by extraction
3. 3
   SecadoThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   Concentraciónconcentrated to dryness under reduced pressure
5. 5
   workup.DISSOLUTIONThe generated residue was dissolved in diethyl ether (130 ml)
6. 6
   workup.ADDITIONConcentrated hydrochloric acid (25 ml) was added to the solution
7. 7
   workup.STIRRINGby stirring for 2 hours
8. 8
   workup.ADDITIONA 5N aqueous sodium hydroxide solution (72 ml) was added to the reaction mixture
9. 9
   Concentraciónfollowed by concentration under reduced pressure
10. 10
    workup.DISSOLUTIONThe residue was dissolved in dichloromethane
11. 11
    Lavadowashed with an aqueous saturated sodium chloride solution
12. 12
    ConcentraciónThe thus-obtained organic layer was concentrated to dryness under reduced pressure
13. 13
    Otrothe generated residue was then purified
14. 14
    ConcentraciónThe purified product was concentrated to dryness under reduced pressure

Procedimiento

To a 5-bromo-6-propoxyindan (8.24 g, 32.2 mmol) toluene solution (80 ml) were added a benzophenone imine (6.40 g, 35.3 mmol) toluene solution (40 ml), tris(dibenzylideneacetone)dipalladium (742 mg, 0.8 mmol), 9,9-dimethyl-4,5-bis (diphenylphosphino)xanthene (XANTPHOS, 936 mg, 1.6 mmol), and cesium carbonate (15.72 g, 48.3 mmol). The resulting mixture was stirred at 100° C. under a nitrogen atmosphere for 47 hours, and then cooled to room temperature. Water and saturated ammonium chloride solution were added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated to dryness under reduced pressure. The generated residue was dissolved in diethyl ether (130 ml). Concentrated hydrochloric acid (25 ml) was added to the solution, followed by stirring for 2 hours. A 5N aqueous sodium hydroxide solution (72 ml) was added to the reaction mixture to adjust its pH to 11, followed by concentration under reduced pressure. The residue was dissolved in dichloromethane and washed with an aqueous saturated sodium chloride solution. The thus-obtained organic layer was concentrated to dryness under reduced pressure, and the generated residue was then purified using silica gel column chromatography (dichloromethane:ethyl acetate=90:1). The purified product was concentrated to dryness under reduced pressure, giving a pale brown oily substance of 6-propoxy-indan-5-ylamine (1.02 g, yield: 17%).

Fuente