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

HRID 1530966Notes

Reaction equation

HRID 1530966 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+].Cl.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34]Cl)[CH:29]=1>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][CH2:34][C:30]5[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=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 2125284210-bromo-2-hydroxy-5-methyl-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 1936487210-bromo-5-methyl-2-(3-pyridylmethyloxy)-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 60.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10-bromo-2-hydroxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-one (350 mg) obtained in Example 49 was suspended in dimethyl sulfoxide (14 ml), and potassium carbonate (440 mg) was added to the suspension. The mixture was stirred at room temperature for 30 minutes and 3-picolylchloride hydrochloride (190 mg) was added to the mixture. The mixture was stirred at room temperature for 12 hours, and the reaction mixture was poured into ice water (500 ml). The crystals precipitated 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 (270 mg, 60%).

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. customThe crystals precipitated
  3. filtrationwere recovered by filtration
  4. washThe resulting crude crystals were washed with methanol and ether in succession
  5. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-7d4089030a954ec8bd1f1168bbf2a7e3
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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