3-(2-Bromoethyl)indole → Indole, 3-(2-(isoindolin-2-yl)ethyl)-

HRID 1095530Notes

Reaction equation

HRID 1095530 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.[CH:13]1[NH:14][CH:15]=[C:16]2[C:21]=1[CH:20]=[CH:19][CH:18]=[CH:17]2>O1CCOCC1>[CH2:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][N:14]1[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

Participants

4

Reactant 2

HCID 769243-(2-Bromoethyl)indoleHCID 3013853Isoindole

Product 1

HCID 39465Indole, 3-(2-(isoindolin-2-yl)ethyl)-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-(2-bromo-ethyl)-1H-indole (4.48 g, 20 mmol) and isoindole (4.76 g, 40 mmol) in abs. dioxane (50 ml) was stirred at 80° C. for 6 h. 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).

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-bc4bcb7578264a7e9adcb73371d5f13f
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…