Reacción #3454

Ecuación de reacción

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

NaH

1-(chloromethyl)naphthalene

→

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

Rendimiento 97.1%

Disolventes

DMF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 5 hours
2. 2
   Extracciónextracted twice with ethyl acetate
3. 3
   LavadoThe combined ethyl acetate was washed with brine
4. 4
   Secadodried (MgSO4)
5. 5
   Concentraciónconcentrated at reduced pressure
6. 6
   OtroThe residue was chromatographed on silica gel
7. 7
   Lavadoeluted with 20% EtOAc/hexane

Procedimiento

4-Methoxy-2-methyl-1H-indole (644 mg, 4 mmol) was dissolved in 10 mL of DMF and 160 mg (4 mmol) of 60% NaH/mineral oil was added. After 0.67 hours, 707 mg (4 mmol) of 1-(chloromethyl)naphthalene was added. After 5 hours, the mixture was diluted with water and extracted twice with ethyl acetate. The combined ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 1.17 g (97% yield) of 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole.

Fuente