p-Toluenesulfonic acid → HCID 9881237, compound

HRID 1609398Notes

Reaction equation

HRID 1609398 reaction equation
[C:1](OC1C(F)=C(F)C(F)=C(F)C=1F)(=[O:5])[C:2]([CH3:4])=O.Cl.[CH3:19][N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:29][C:30](=[NH:35])[O:31]C(C)C)=[CH:21]1.C(N(CC)CC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH3:4][C:2]1[C:1](=[O:5])[NH:31][C:30](=[O:35])[C:29]=1[C:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:20]([CH3:19])[CH:21]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 20084657HCID 20084657, compoundHCID 22907276Isopropyl 1-methyl-3-indoleacetimidate hydrochloride

Product 1

HCID 9881237HCID 9881237, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 802 mg of pentafluorophenyl pyruvate in 20 ml of dichloromethane was added dropwise to a solution of 266 mg (1 mmol) of isopropyl 1-methyl-3-indoleacetimidate hydrochloride and 808 mg (8 mmol) of triethylamine in 20 ml of dichloromethane. After completion of the addition, the mixture was stirred at room temperature for 18 hours. Then, 1.9 g (10 mmol) of p-toluenesulfonic acid were added and stirring was continued for 1 hour. The solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel using ethyl acetate/dichloromethane (1:8) for the elution to give 24 mg(10% ) of 3-methyl-4-(1 -methyl-3-indolyl)- 1H-pyrrole-2,5-dione in the form of a yellow solid of melting point 181° C.

Workup

  1. additionAfter completion of the addition
  2. stirringstirring
  3. waitwas continued for 1 hour
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-62b9a34d0cd24c01b8cd55273d9c193e
Source dataset
uspto-grants-1995_03
Patent number
US05399712

Reaction notes

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