Isoquinoline → HCID 10912790, compound

HRID 1095531Notes

Reaction equation

HRID 1095531 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[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1>O1CCOCC1>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][N:14]2[CH2:15][CH2:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)=[CH:5]1

Participants

4

Reactant 2

HCID 8405IsoquinolineHCID 769243-(2-Bromoethyl)indole

Product 1

HCID 10912790HCID 10912790, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-(2-bromo-ethyl)-1H-indole (4.48 g, 20 mmol) and isoquinoline (5.33 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 (50:1). Yield: 4.78 g (Ind-65, 86%), white 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 (50:1)

Sources & evidence

ORD record
ord-a54fc9215a98438d9294c81228e92574
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…