Indole → 1H-Pyrrole-2,5-dione, 3-(1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)-

HRID 440165Notes

Reaction equation

HRID 440165 reaction equation
Br[C:2]1[C:3]([NH:5][C:6](=[O:17])[C:7]=1[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4].[CH2:18]([Mg]Br)C.[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1.BrC1C(=O)NC(=O)C=1Br.[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([C:2]2[C:3]([NH:5][C:6](=[O:17])[C:7]=2[C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:18])[CH:9]=2)=[O:4])=[CH:23]1

Participants

9

Reactant 5

HCID 798IndoleHCID 14279DibromomaleimideHCID 25517Ammonium ChlorideHCID 104695051H-Pyrrole-2,5-dione, 3-bromo-4-(1H-indol-3-yl)-HCID 178418443HCID 178418443, compound

Product 1

HCID 53276541H-Pyrrole-2,5-dione, 3-(1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)-

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The 2-bromo-3-(1H-indol-3-yl)-maleinimide used as starting material is prepared as follows: A solution of 49.3 mmol ethyl magnesium bromide in 30 ml tetrahydrofuran is mixed with a solution of 5.8 g (49.5 mmol) indole in 50 ml toluene. The reaction mixture is stirred for 1 hour at ambient temperature, a solution of 2.5 g (9.8 mmol) dibromomaleinimide in 20 ml tetrahydrofuran/50 ml toluene is then slowly added dropwise thereto and heated under reflux for 30 hours. After cooling, the reaction mixture is decomposed with a saturated aqueous solution of ammonium chloride, the products are extracted with ethyl acetate and the organic phase is subsequently dried over anhydrous sodium sulphate. After evaporation, the red residue obtained is triturated with a little dichloromethane, filtered off with suction and dried in a vacuum at 0.1 Torr and 70° C. There are obtained 2.2 g (75% of theory) of orange-coloured product; m.p. 196° C.; RF=0.35 (hexane/ethyl acetate 1:1 v/v).

Workup

  1. customis prepared
  2. temperatureheated
  3. temperatureunder reflux for 30 hours
  4. temperatureAfter cooling
  5. extractionthe products are extracted with ethyl acetate
  6. dry with materialthe organic phase is subsequently dried over anhydrous sodium sulphate
  7. customAfter evaporation
  8. customthe red residue obtained
  9. customis triturated with a little dichloromethane
  10. filtrationfiltered off with suction
  11. customdried in a vacuum at 0.1 Torr and 70° C
  12. customThere are obtained 2.2 g (75% of theory) of orange-coloured product

Sources & evidence

ORD record
ord-cf3b095f93fc4150a858029a7a67a5a2
Source dataset
uspto-grants-1996_05
Patent number
US05516915

Reaction notes

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