6-Phenyl-1,3-dihydro-indol-2-one → 3-[2-(2-Oxo-6-phenyl-1,2-dihydro-indol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acid

HRID 24517Notes

Reaction equation

HRID 24517 reaction equation
[C:1]1([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17]([C:19]1[NH:20][C:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=2[C:27]=1[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=O>N1CCCCC1.C(O)C>[O:16]=[C:12]1[C:11](=[CH:17][C:19]2[NH:20][C:21]3[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=3[C:27]=2[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:10]2[C:14](=[CH:15][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=2)[NH:13]1

Participants

5

Reactant 2

HCID 105363846-Phenyl-1,3-dihydro-indol-2-oneHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid

Product 1

HCID 697629183-[2-(2-Oxo-6-phenyl-1,2-dihydro-indol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]-propionic acidYield 33.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 90 mg 6-phenyl-2-oxindole, 95 mg 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid and piperidine ( 3 drops) in ethanol (2 mL) was held in a sealed tube at 90° C. for 4 hrs. The reaction mixture was concentrated and acidified with 6 N hydrochloric acid. The precipitate was collected by filtration and washed with water and hexane to give 59 mg of 3-[2-(2-oxo-6-phenyl-1,2-dihydro-indol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3yl]-propionic acid as a brown solid (31% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water and hexane

Sources & evidence

ORD record
ord-c27a972ea62542709731c61b26e8a290
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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