Ethyl bromoacetate → 10-bromo-2-ethoxycarbonylmethyloxy-4H-pyrido [3,2,1-jk]carbazole-4-one

HRID 1530973Notes

Reaction equation

HRID 1530973 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][CH2:31][CH3:32])=[O:29]>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][CH2:31][CH3:32])=[O:29])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 2125288410-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 2125284410-bromo-2-ethoxycarbonylmethyloxy-4H-pyrido [3,2,1-jk]carbazole-4-oneYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one (400 mg) obtained in Example 59 was suspended in dimethyl sulfoxide (10 ml), and potassium carbonate (0.34 g) was added to the suspension. The mixture was stirred at room temperature for 30 minutes and ethyl bromoacetate (0.15 ml) was added to the mixture. The mixture was stirred at room temperature for 12 hours, and the reaction mixture was poured into ice water (50 ml), and the crystals precipitated were recovered by filtration. The crude crystals obtained were washed with water, ethanol and ether in succession, and recovered by filtration to obtain the title compound (410 mg, 84%).

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 obtained
  5. washwere washed with water, ethanol and ether in succession
  6. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-0dc0203b85af49fa9c9186094596041e
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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