Potassium Carbonate → 9-bromo-5-(3-pyridylmethyl)-2-(3-pyridylmethyloxy)-4H-pyrido [3,2,1-jk]carbazole-4-one

HRID 1530986Notes

Reaction equation

HRID 1530986 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:16](=[O:26])[C:17]([CH2:19][C:20]5[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=5)=[CH:18][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([OH:15])[CH:10]=3.C(=O)([O-])[O-].[K+].[K+].[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39]Cl)[CH:34]=1>CS(C)=O>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:16](=[O:26])[C:17]([CH2:19][C:20]5[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=5)=[CH:18][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH2:39][C:35]1[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=1)[CH:10]=3

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 183583-(Chloromethyl)pyridineHCID 212528709-bromo-2-hydroxy-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 193649179-bromo-5-(3-pyridylmethyl)-2-(3-pyridylmethyloxy)-4H-pyrido [3,2,1-jk]carbazole-4-oneYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

9-bromo-2-hydroxy-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one (200 mg) produced in Example 102 was suspended in dimethyl sulfoxide (8 ml). After adding potassium carbonate (204 mg), the mixture was stirred at room temperature for 30 minutes, and 3-picolylchloride (0.09 ml) was added. After stirring at room temperature for 12 hours, the reaction mixture was poured into ice water (20 ml) and the crystals precipitated were recovered by filtration. The thus obtained crude crystals were washed with water, ethanol and ether in succession and recovered by filtration to obtain the title compound (177 mg, 72%).

Workup

  1. stirringAfter stirring at room temperature for 12 hours
  2. customthe crystals precipitated
  3. filtrationwere recovered by filtration
  4. customThe thus obtained crude crystals
  5. washwere washed with water, ethanol and ether in succession
  6. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-3ec7467e889548ac892fecbc6f865e8f
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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