Bromobenzene → HCID 21891628, compound

HRID 720336Notes

Reaction equation

HRID 720336 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:16]([O:18][CH3:19])=[O:17])[NH:7]2.Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[K+]>CN(C=O)C.O.[Cu]=O>[C:21]1([N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=3)[CH:5]=[C:6]2[C:16]([O:18][CH3:19])=[O:17])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 7961BromobenzeneHCID 14797Potassium HydroxideHCID 4715372VGRVYVYBENLQJG-UHFFFAOYSA-N

Product 1

HCID 21891628HCID 21891628, compound

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 4,5,6-trimethoxyindole-2-carboxylate (533 mg), bromobenzene (0.22 mL), copper oxide (64 mg) and potassium hydroxide (336 mg) were suspended in dry DMF (10 mL), and the suspension was refluxed and stirred for 6 hours under an argon atmosphere. After cooling, the reaction mixture was dissolved in water (100 mL) and filtered through celite. The filtrate was extracted with ethyl acetate, and the extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was dissolved in methanol (20 mL) and chloroform (20 mL), and water-soluble carbodiimide hydrochloride (192 mg) and N,N-dimethylaminopyridine (small amount) were added to the solution. The mixture was stirred overnight at room temperature. After concentrating the reaction mixture under reduced pressure, water was added to the residue to conduct extraction with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by preparative TLC on silica gel (ethyl acetate:hexane=1:3) to obtain the title compound.

Workup

  1. temperaturethe suspension was refluxed
  2. temperatureAfter cooling
  3. filtrationfiltered through celite
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe extract was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in methanol (20 mL)
  9. additionchloroform (20 mL), and water-soluble carbodiimide hydrochloride (192 mg) and N,N-dimethylaminopyridine (small amount) were added to the solution
  10. stirringThe mixture was stirred overnight at room temperature
  11. concentrationAfter concentrating the reaction mixture under reduced pressure, water
  12. additionwas added to the residue
  13. extractionextraction with ethyl acetate
  14. washThe resultant organic layer was washed with water and saturated brine
  15. dry with materialdried over anhydrous magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customThe residue was purified by preparative TLC on silica gel (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-4cfc930c59dc4c2984c6d26346c9cc66
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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