Indole → HCID 15422868, compound

HRID 345667Notes

Reaction equation

HRID 345667 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C[Mg]I.Br[C:14]1[C:15](=[O:26])[NH:16][C:17](=[O:25])[C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1C=CC=CC=1.C(OCC)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:14]2[C:15](=[O:26])[NH:16][C:17](=[O:25])[C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:2]1

Participants

6

Reactant 3

HCID 798IndoleHCID 22289789HCID 22289789, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 15422868HCID 15422868, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.9 g of indole in 50 ml of benzene was treated with 19 ml of a 3M solution of methylmagnesium iodide in diethyl ether and stirred under nitrogen for 15 minutes. 3.5 g of 3-bromo-4-phenyl-1H-pyrrole-2,5-dione were added and the mixture was stirred for 18 hours. The solvent was evaporated and the residue was dissolved in 250 ml of dichloromethane and 50 ml of 2M hydrochloric acid. The organic extracts were washed with water, dried and evaporated. The residue was purified on silica gel with ethyl acetate/petroleum ether. Trituration with dichloromethane and recrystallization from methanol yielded 1.40 g of 3-(3-indolyl)-4-phenyl-1H-pyrrole-2,5-dione, m.p. 256° C.

Workup

  1. stirringthe mixture was stirred for 18 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in 250 ml of dichloromethane
  4. washThe organic extracts were washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was purified on silica gel with ethyl acetate/petroleum ether
  8. customTrituration with dichloromethane and recrystallization from methanol

Sources & evidence

ORD record
ord-85ecb27d6a8b473dafe2153d9e775497
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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