Benzyl Bromide → Indole

HRID 2303524Notes

Reaction equation

HRID 2303524 reaction equation
C([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+]([O-])=O)[CH:8]=[CH:7][CH:6]=2)C.[H-].[Na+].CCCCCC.C(Br)C1C=CC=CC=1>CN(C=O)C.O>[NH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:3]1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 24758Sodium hydrideHCID 130479942-ethyl-4-nitro-1H-indole

Product 1

HCID 798Indole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2-Ethyl -4-nitro-1H-indole (4.75 g, 25 mmol) was added to a mixture of 1.0 g (25 mmol) of 60% NaH/mineral oil (washed with hexane before adding DMF) in 40 ml DMF. After 45 minutes, 3.0 ml (25 mmol) of benzyl bromide was added. The mixture was stirred at room temperature for four hours, diluted with water, and extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 20% EtOAc/Hexane to give 6.36 g (91%) of 1-Phenylmethyl-2-ethyl-4-nitro]1H-indole as an oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe EtOAc solution was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 20% EtOAc/Hexane

Sources & evidence

ORD record
ord-7cd6351868604ab7a42fad4335807665
Source dataset
uspto-grants-2002_08
Patent number
US06433001B1

Reaction notes

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