Imidazole → 3-(2-(1H-Imidazol-1-yl)ethyl)-1H-indole

HRID 1095536Notes

Reaction equation

HRID 1095536 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>O1CCOCC1>[N:13]1([CH2:2][CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 769243-(2-Bromoethyl)indole

Product 1

HCID 574751493-(2-(1H-Imidazol-1-yl)ethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-(2-bromo-ethyl)-1H-indole (1.12 g, 5 mmol) and imidazole (0.68 g, 10 mmol) in abs. dioxane (10 ml) was stirred at 80° C. for 4 h until according to TLC educt was no longer present. The solvent was then removed i. vac., CHCl3 (100 ml) was added to the residue and the mixture was washed twice with water. The organic phase was dried over Na2SO4 and concentrated i. vac. and the residue which remained was purified by flash chromatography with CHCl3/MeOH (20:1). Yield: 507 mg (Ind-71, 48%), colourless solid

Workup

  1. customThe solvent was then removed i
  2. addition, CHCl3 (100 ml) was added to the residue
  3. washthe mixture was washed twice with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated i
  6. customand the residue which remained was purified by flash chromatography with CHCl3/MeOH (20:1)

Sources & evidence

ORD record
ord-1cd6c2ba24324ef5b32ba69082d4c40e
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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