Benzimidazole → 1-(2-(5-Fluoro-1H-indol-3-yl)ethyl)-1H-benzo[d]imidazole

HRID 1095512Notes

Reaction equation

HRID 1095512 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:13])[CH:11]=2)[NH:6][CH:5]=1.[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][CH:15]=1.C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl>[F:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][CH:5]=[C:4]2[CH2:3][CH2:2][N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 81531DiisopropylethylamineHCID 112072263-(2-bromoethyl)-5-fluoro-1H-indole

Product 1

HCID 574751361-(2-(5-Fluoro-1H-indol-3-yl)ethyl)-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3-(2-bromo-ethyl)-5-fluoro-1H-indole (7.26 g, 30 mmol), benz-imidazole (3.54 g, 30 mmol) and ethyl-diisopropylamine (5.1 ml, 30 mmol) in abs. chloroform (80 ml) was boiled under reflux for 20 h. The reaction solution was then washed twice with water, dried over Na2SO4 and concentrated i. vac. and the residue which remained was purified by flash chromatography with CHCl3/MeOH (50:1).

Workup

  1. temperatureunder reflux for 20 h
  2. washThe reaction solution was then washed twice with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated i
  5. customand the residue which remained was purified by flash chromatography with CHCl3/MeOH (50:1)

Sources & evidence

ORD record
ord-4ed505e822d24eb8942958a5e2ee990d
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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