Reacción #3450

Ecuación de reacción

4-fluorobenzyl chloride

4-Methoxy-2-methyl-1H-indole

sodium hydride

hexane

→

1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole

Rendimiento 84.0%

Disolventes

water

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 18 hours
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   LavadoThe ethyl acetate solution was washed with brine
4. 4
   Secadodried (MgSO4)
5. 5
   Concentraciónafter concentrating at reduced pressure
6. 6
   Otrothe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Procedimiento

4-Methoxy-2-methyl-1H-indole (805 mg, 5 mmol) was added to a mixture of 200 mg (5 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 10 mL of DMF and after stirring for 0.5 hours, 0.6 mL (5 mmol) of 4-fluorobenzyl chloride was added. The mixture was stirred at room temperature for 18 hours, diluted with water-and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4) and after concentrating at reduced pressure, the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.1 g (84% yield) of 1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole, melting at 104°-108° C.

Fuente