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

HRID 1530975Notes

Reaction equation

HRID 1530975 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+].Cl.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]Cl)[CH:28]=1>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][CH2:33][C:29]5[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=5)[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 2125288410-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 1936491610-bromo-2-(3-pyridylmethyloxy)-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 52%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one (300 mg) obtained in Example 59 was suspended in dimethyl sulfoxide (20 ml), and potassium carbonate (400 mg) was added to the suspension. The mixture was stirred at room temperature for 30 minutes and 3-picolylchloride hydrochloride (180 mg) was added and the mixture was, stirred at room temperature for 12 hours. The reaction mixture was poured into ice water (100 ml), and the precipitated crystals were recovered by filtration. The resulting crude crystals were washed with methanol and ether in succession, and recovered by filtration to obtain the title compound (200 mg, 52%).

Workup

  1. stirringstirred at room temperature for 12 hours
  2. filtrationthe precipitated crystals were recovered by filtration
  3. washThe resulting crude crystals were washed with methanol and ether in succession
  4. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-1291b360517148ceb3e7bee58fc5f15a
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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