Potassium Iodide → 10-bromo-2-(4-hydroxybutyloxy)-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 850771Notes

Reaction equation

HRID 850771 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[CH:17][C:16](=[O:19])[C:8]4[CH:9]=[C:10]([OH:15])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:27][CH2:28][CH2:29][CH2:30][OH:31].[I-].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[CH:17][C:16](=[O:19])[C:8]4[CH:9]=[C:10]([O:15][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 135694-Chloro-1-butanolHCID 2125288410-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 1936492310-bromo-2-(4-hydroxybutyloxy)-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 52%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one (250 mg) obtained in Example 59 was suspended in dimethyl sulfoxide (12 ml), and potassium carbonate (220 mg) was added to the suspension. The mixture was stirred at room temperature for 30 minutes and 4-chloro-1-butanol (0.095 ml) and potassium iodide (1 grain) were added to the mixture. The mixture was stirred at 80° C. in a hot water bath for 24 hours, and the reaction mixture was poured into ice water (100 ml), and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: methylene chloride/methanol=20:1) to obtain the title compound (160 mg, 52%).

Workup

  1. stirringThe mixture was stirred at 80° C. in a hot water bath for 24 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel flash column chromatography (eluent: methylene chloride/methanol=20:1)

Sources & evidence

ORD record
ord-53043e8b0b5a431ea21f04d8131b55e8
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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