p-Toluenesulfonic acid → 1H-Pyrrole-2,5-dione, 3,4-bis(1-methyl-1H-indol-3-yl)-

HRID 1609396Notes

Reaction equation

HRID 1609396 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=O)[C:12]([O:14]C2C(F)=C(F)C(F)=C(F)C=2F)=O)=[CH:3]1.Cl.[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH2:38][C:39](=[NH:44])[O:40]C(C)C)=[CH:30]1.C(N(CC)CC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([C:38]2[C:39](=[O:40])[NH:44][C:12](=[O:14])[C:11]=2[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[CH:30]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 22907276Isopropyl 1-methyl-3-indoleacetimidate hydrochlorideHCID 53704947HCID 53704947, compound

Product 1

HCID 53276551H-Pyrrole-2,5-dione, 3,4-bis(1-methyl-1H-indol-3-yl)-Yield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 369 mg (1 mmol) of pentafluorophenyl 1-methylindole-3-glyoxylate in 20 ml of dichloromethane was added to a stirred solution of 266 mg (1 mmol) of isopropyl 1-methyl-3-indoleacetimidate hydrochloride and 404 mg (4 mmol) of triethylamine in 25 ml of dichloromethane. The solution obtained was heated to reflux under nitrogen for 18 hours, cooled and treated with 950 mg (5 mmol) of p-toluenesulfonic acid. After 1 hour, the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel using dichloromethane/ethyl acetate (8:1) for the elution to give 159mg (45%) of 3,4-bis-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione in the form of an orange colored solid of melting point >310° C.

Workup

  1. customThe solution obtained
  2. temperaturewas heated
  3. temperatureto reflux under nitrogen for 18 hours
  4. temperaturecooled
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-27fc19f7c2da4f72bd2dc55ed9ea8e20
Source dataset
uspto-grants-1995_03
Patent number
US05399712

Reaction notes

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