Potassium Carbonate → l0-bromo-2-t-butoxycarbonylmethyloxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 850755Notes

Reaction equation

HRID 850755 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+].Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>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][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 2125284210-bromo-2-hydroxy-5-methyl-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 9824608l0-bromo-2-t-butoxycarbonylmethyloxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 39%

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 t-butyl bromoacetate (0.13 ml) was added to the mixture. The mixture was stirred for 2.5 hours at room temperature, and 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 column chromatography (eluent: methylene chloride containing 2% methanol), and the crude purification product was washed with ether and recovered by filtration to obtain the title compound (130 mg, 39%).

Workup

  1. stirringThe mixture was stirred for 2.5 hours at room temperature
  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 2% methanol)
  7. customthe crude purification product
  8. washwas washed with ether
  9. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-426c7bb4e6e9438ba8a63a43f857d463
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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