Sodium Carbonate → 2-(2-(2-(3,5-Dimethylphenyl)-1H-indol-3-yl)ethyl)isoindoline-1,3-dione

HRID 1292374Notes

Reaction equation

HRID 1292374 reaction equation
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][N:13]1[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]1=[O:23])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([CH3:31])[CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:24][C:25]1[CH:26]=[C:27]([C:2]2[NH:3][C:4]3[C:9]([C:10]=2[CH2:11][CH2:12][N:13]2[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]2=[O:23])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:28]=[C:29]([CH3:31])[CH:30]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27343493,5-Dimethylphenylboronic acidHCID 109706542-[2-(2-bromo-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione

Product 1

HCID 153130482-(2-(2-(3,5-Dimethylphenyl)-1H-indol-3-yl)ethyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-[2-(2-bromo-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione (150 mg in a mixture of 5 mL toluene and 5 mL ethanol) was added 3,5-dimethylphenyl boronic acid (85 mg) followed by 1.0 mL of 1M sodium carbonate. To the stirred solution was added lithium chloride (60 mg) followed by tetrakis(triphenylphosphine) palladium (28 mg) and the mixture heated to reflux on an oil bath. After 4 hours the mixture was cooled to room temperature and concentrated in vacuo. Purification by flash chromatography on silica gel (hexane:ethyl acetate, 5:1) gave the title compound (146 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography on silica gel (hexane:ethyl acetate, 5:1)

Sources & evidence

ORD record
ord-7ebcaee8281f49a9ad5c93730cd4e890
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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