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

HRID 1530977Notes

Reaction equation

HRID 1530977 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+].Br[CH2:27][C:28](=[O:32])[CH2:29][CH2:30][CH3:31]>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][C:28](=[O:32])[CH2:29][CH2:30][CH3:31])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 100578691-Bromopentan-2-oneHCID 2125288410-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 1936487310-bromo-2-(2-oxopentyloxy)-4H-pyrido [3,2,1-jk]carbazole-4-oneYield 41%

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 (10 ml), and potassium carbonate (210 mg) was added to the suspension. The mixture was stirred at room temperature for 30 minutes and 1-bromo-2-pentanone (170 mg) was added to the mixture. The mixture was stirred at room temperature for 3 hours, and the reaction mixture was poured into ice water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, 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 containing 2% methanol) to obtain the title compound (130 mg, 41%).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 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 containing 2% methanol)

Sources & evidence

ORD record
ord-ff569f01db2d445f8bc370e5a15c9b9e
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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