Potassium Iodide → 10-bromo-5-methyl-2-i-propoxycarbonylmethyloxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 850756Notes

Reaction equation

HRID 850756 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)[C:8]4[CH:9]=[C:10]([OH:15])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.[C:21](=[O:24])([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30].[I-].[K+]>CS(C)=O>[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]3[CH2:18][C:17]([CH3:19])([CH2:16][C:8]4[CH:7]=[N:6][CH:18]=[CH:17][CH:16]=4)[C:21](=[O:24])[C:12]4[CH:11]=[C:10]([O:15][CH2:28][C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH:9]=[C:8]([C:4]=2[CH:3]=1)[C:7]3=4

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 121593Isopropyl bromoacetateHCID 2125284210-bromo-2-hydroxy-5-methyl-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 1936489310-bromo-5-methyl-2-i-propoxycarbonylmethyloxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 67%

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 i-propyl bromoacetate (0.12 ml) and potassium iodide (1 grain) were added in succession, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into ice water (50 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: ethyl acetate), and the crude purification product was washed with ether and recovered by filtration to obtain the title compound (220 mg, 67%).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 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: ethyl acetate)
  7. customthe crude purification product
  8. washwas washed with ether
  9. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-e78a6e8adf514b3aa2286388a3aaaa0c
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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