Potassium Iodide → N-Benzyl-6,6-dimethyl-1H-pyrano[2,3-f]indole-2,3-dione

HRID 2425370Notes

Reaction equation

HRID 2425370 reaction equation
[CH2:1]([N:8]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[C:11](=[O:12])[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[C:29]([CH3:33])([CH3:32])[C:30]#[CH:31].[Cl-].[NH4+]>CN(C=O)C.[Cu](I)I>[CH2:1]([N:8]1[C:18]2[C:13](=[CH:14][C:15]3[O:19][C:29]([CH3:33])([CH3:32])[CH:30]=[CH:31][C:16]=3[CH:17]=2)[C:11](=[O:12])[C:9]1=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 706791-Butyne, 3-chloro-3-methyl-HCID 59134289N-Benzyl-5-hydroxyisatin

Product 1

HCID 59134332N-Benzyl-6,6-dimethyl-1H-pyrano[2,3-f]indole-2,3-dioneYield 8%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

Under nitrogen stream, a solution of N-benzyl-5-hydroxyisatin (4.74 g, 18.7 mmol), potassium iodide (5.09 g, 31.8 mmol), potassium carbonate (5.17 g, 37.4 mmol), copper iodide (71 mg, 0.37 mmol) and 3-chloro-3-methyl-1-butyne (4.83 mL, 43.0 mmol) in DMF (47 mL) was stirred at 70° C. for 2 hours. Upon the completion of the reaction, saturated ammonium chloride aqueous solution was added thereto, the resulting solution was extracted with ethyl acetate. The resulting organic phase was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated and purified by silica gel short column (chloroform). 1,2-Dichlorobenzene (9 mL) was added and the resulting mixture was stirred at 200° C. for 30 minutes. After concentrating the reaction solution, the residue was purified by silica gel column (hexane/ethyl acetate=5/1) to obtain the aimed product (yield: 8%).

Workup

  1. additionwas added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe resulting organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel short column (chloroform)
  7. addition1,2-Dichlorobenzene (9 mL) was added
  8. concentrationAfter concentrating the reaction solution
  9. customthe residue was purified by silica gel column (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-325fdad345cf498d815f53c290d6fe5b
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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