Potassium Carbonate → 10-bromo-2-(4-hydroxybutyloxy)-5-methyl-4H-pyrido [3,2,1-jk]carbazole-4-one

HRID 850760Notes

Reaction equation

HRID 850760 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[C:17]([CH3:19])[C:16](=[O:20])[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[CH2:28][CH2:29][CH2:30][CH2:31][OH:32]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[C:17]([CH3:19])[C:16](=[O:20])[C:8]4[CH:9]=[C:10]([O:15][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135694-Chloro-1-butanolHCID 2125284210-bromo-2-hydroxy-5-methyl-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 1936492510-bromo-2-(4-hydroxybutyloxy)-5-methyl-4H-pyrido [3,2,1-jk]carbazole-4-oneYield 26%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10-bromo-2-hydroxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-one (250 mg) obtained in Example 49 was suspended in dimethyl sulfoxide (10 ml), and potassium carbonate (210 mg) was added to the suspension. The mixture was stirred at room temperature for 30 minutes and 4-chloro-1-butanol (0.09 ml) was added to the mixture. The mixture was stirred at 80° C. in a hot water bath for 14 hours, and the reaction mixture was poured into ice water (500 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 column chromatography (eluent: methylene chloride containing 4% methanol) to obtain the title compound (80 mg, 26%).

Workup

  1. stirringThe mixture was stirred at 80° C. in a hot water bath for 14 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 column chromatography (eluent: methylene chloride containing 4% methanol)

Sources & evidence

ORD record
ord-e5fb54472f8146acae04f6927a1d82bc
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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