Indole → HCID 14855724, compound

HRID 345668Notes

Reaction equation

HRID 345668 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]Br.Br[C:14]1[C:15](=[O:31])[NH:16][C:17](=[O:30])[C:18]=1[C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=2)[NH: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:31])[NH:16][C:17](=[O:30])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[CH:26]=3)[NH:21][CH:20]=2)=[CH:2]1

Participants

6

Reactant 3

HCID 798IndoleHCID 18780286HCID 18780286, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 14855724HCID 14855724, compoundYield 2.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 105 mg of indole in 20 ml of benzene were added 0.6 ml of a 3M solution of methylmagnesium bromide in diethyl ether under nitrogen. The mixture was stirred for 0.5 hour. 100 mg of 3-bromo-4-(5-methoxy-3-indolyl)-1H-pyrrole-2,5-dione were added and the mixture was heated to reflux for 5 days. After cooling the residue was partitioned between dichloromethane and 2M hydrochloric acid. The organic extracts were washed with water, dried and evaporated. The residue was purified on silica gel with 1% methanol in dichloromethane and then with 50% methanol/0.1% trifluoroacetic acid/water on Spherisorb to give 3 mg of 3-(3-indolyl)-4-(5-methoxy-3-indolyl)-1H-pyrrole-2,5-dione, m.p. 280° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 days
  3. temperatureAfter cooling the residue
  4. customwas partitioned between dichloromethane and 2M hydrochloric acid
  5. washThe organic extracts were washed with water
  6. customdried
  7. customevaporated
  8. customThe residue was purified on silica gel with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-29cb33cab90848fba678c81134a87cfb
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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