Isatin → 1-(3-Thienyl)-1H-indole-2,3-dione

HRID 218093Notes

Reaction equation

HRID 218093 reaction equation
C(N(CC)CC)C.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[C:9]1=[O:18].[S:19]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20]1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[S:19]1[CH:23]=[CH:22][C:21]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[C:9]2=[O:18])=[CH:20]1

Participants

6

Reactant 3

HCID 7054IsatinHCID 8471TriethylamineHCID 581760Thiophene-3-boronic acid

Product 1

HCID 220224311-(3-Thienyl)-1H-indole-2,3-dioneYield 50%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (56.9 mL, 0.408 mol), was added to a mixture of 1H-indole-2,3-dione (15.0 g, 0.102 mol), copper (II) acetate (46.0 g, 0.255 mol), and 3-thienylboronic acid (19.6 g, 0.153 mol) in CH2Cl2 (500 mL). The reaction mixture was stirred overnight, filtered through Celite, rinsed with EtOAc/hexane (1:1, 300 mL), and concentrated in vacuo. The crude product was purified by column chromatography on silica using Hexane/EtOAc (1:1), giving the desired product (1.1 g, 50%).

Workup

  1. filtrationfiltered through Celite
  2. washrinsed with EtOAc/hexane (1:1, 300 mL)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography on silica

Sources & evidence

ORD record
ord-4bc4166cc7d24e6d87fe326e88be6c96
Source dataset
uspto-grants-2012_06
Patent number
US08198313B2

Reaction notes

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