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

HRID 566641Notes

Reaction equation

HRID 566641 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:12])[NH:7]2.[H-].[Na+].[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH3:21]N(C=O)C>O.C(Br)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:12])[N:7]2[CH2:21][C:17]1[CH:16]=[CH:15][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 8058HexaneHCID 24758Sodium hydrideHCID 107732744-methoxy-2-methyl-1H-indole

Product 1

HCID 107771474-methoxy-2-methyl-1-(phenylmethyl)-1H-indoleYield 84%

Reagents, catalysts & solvents 2

HCID 7498Benzyl BromideCatalystHCID 962WaterSolvent

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 nmol) 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.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationafter concentrating at reduced pressure
  6. customthe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-2188d1fd16544025ae24d761b5795a20
Source dataset
uspto-grants-2001_01
Patent number
US06175021B1

Reaction notes

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