Potassium Carbonate → 10-bromo-2-(2-oxobutyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 850750Notes

Reaction equation

HRID 850750 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[C:17]([CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:16](=[O:26])[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[CH2:34][C:35](=[O:38])[CH2:36][CH3:37]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[C:17]([CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:16](=[O:26])[C:8]4[CH:9]=[C:10]([O:15][CH2:34][C:35](=[O:38])[CH2:36][CH3:37])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131561-Bromo-2-butanoneHCID 1588691010-bromo-2-hydroxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 1936490210-bromo-2-(2-oxobutyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10-bromo-2-hydroxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (0.3 g) obtained in Example 2 was suspended in dimethyl sulfoxide (20 ml), and to the suspension was added potassium carbonate (0.2 g), and the mixture was stirred at room temperature for 30 minutes. 1-bromo-2-butanone (0.1 ml) was added and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into ice water, and the precipitated crystals were recovered by filtration. The resulting crude crystals were washed with methanol and ethanol in succession to obtain the title compound (192 mg, 55%).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. filtrationthe precipitated crystals were recovered by filtration
  3. washThe resulting crude crystals were washed with methanol and ethanol in succession

Sources & evidence

ORD record
ord-27d91a7650464107a0f51ca97ee87b49
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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