Reaction #3433

Reaction equation

benzyl bromide

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

sodium hydride

hexane

→

4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole

Yield 84.0%

Solvents

water

DMF

DMF

Conditions

Workup

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

Procedure

4-Methoxy-2-methyl-1H-indole (1 g, 6.2 mmol) was added to 248 mg (6.2 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 15 mL of DMF and after stirring for 0.5 hour, 0.74 mL (6.2 mmol) of benzyl bromide 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 1.3 g (84% yield) of 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole, melting at 96°-116° C.

Source