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

HRID 1530972Notes

Reaction equation

HRID 1530972 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:30][CH:31]([CH3:33])[CH3:32])=[O:29].[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][C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 121593Isopropyl bromoacetateHCID 2125288410-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 1936491110-bromo-2-i-propoxycarbonylmethyloxy-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 51%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one (3 g) obtained in Example 59 was suspended in dimethyl sulfoxide (120 ml), and potassium carbonate (2.6 g) was added to the suspension. The mixture was stirred at room temperature for 30 minutes and i-propyl bromoacetate (1.4 ml) and potassium iodide (1 grain) were added in succession to the mixture. The mixture was stirred at room temperature for 12 hours, and the reaction mixture was poured into ice water (500 ml), and the crystals precipitated were recovered by filtration. The crude crystals were purified by silica gel flash column chromatography (eluent: methylene chloride containing 1% methanol) to obtain the title compound (2.0 g, 51%).

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. customthe crystals precipitated
  3. filtrationwere recovered by filtration
  4. customThe crude crystals were purified by silica gel flash column chromatography (eluent: methylene chloride containing 1% methanol)

Sources & evidence

ORD record
ord-a5bae7b1b82a4a3db1688c8d6d344b4e
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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