2-{4-[2-(Benzhydryl-amino)-5-chloro-phenyl]-but-3-ynyl}-isoindole-1,3-dione → 2-[2-(1-Benzhydryl-5-chloro-1H-indol-2-yl)-ethyl]-isoindole-1,3-dione

HRID 1392597Notes

Reaction equation

HRID 1392597 reaction equation
[CH:1]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[C:22]#[C:23][CH2:24][CH2:25][N:26]1[C:34](=[O:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]1=[O:36])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN(C)C=O.[Cu](I)I>[CH:1]([N:14]1[C:15]2[C:16](=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH:22]=[C:23]1[CH2:24][CH2:25][N:26]1[C:27](=[O:36])[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]1=[O:35])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 113863132-{4-[2-(Benzhydryl-amino)-5-chloro-phenyl]-but-3-ynyl}-isoindole-1,3-dione

Product 1

HCID 112488722-[2-(1-Benzhydryl-5-chloro-1H-indol-2-yl)-ethyl]-isoindole-1,3-dioneYield 95%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{4-[2-(Benzhydryl-amino)-5-chloro-phenyl]-but-3-ynyl}-isoindole-1,3-dione made in Example 2 (13.1 g, 26.7 mmol) in dimethylformamide (65 ml) at ambient temperature was added copper iodide (1.02 g, 5.3 mmol). The reaction mixture suspension was heated at 120 C for 16 h. Then it was heated at 140 C for 4 h. The reaction mixture was filtered at 60° C. Water (200 ml) was added to the filtrate. The product was collected after filtration and washing with water (20 ml×4). Drying the product in vacuo at 60° C. provided an off-white solid product, 2-[2-(1-Benzhydryl-5-chloro-1H-indol-2-yl)-ethyl]-isoindole-1,3-dione (12.5 g, yield 95%). HPLC (area %): 97.3%

Workup

  1. temperatureThe reaction mixture suspension was heated at 120 C for 16 h
  2. temperatureThen it was heated at 140 C for 4 h
  3. filtrationThe reaction mixture was filtered at 60° C
  4. additionWater (200 ml) was added to the filtrate
  5. customThe product was collected
  6. filtrationafter filtration
  7. washwashing with water (20 ml×4)
  8. customDrying the product in vacuo at 60° C.

Sources & evidence

ORD record
ord-15b6aca1e9b4418e8d8b54241cea0698
Source dataset
uspto-grants-2008_03
Patent number
US07342119B2

Reaction notes

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