Potassium Carbonate → HCID 19364901, compound

HRID 850787Notes

Reaction equation

HRID 850787 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:20])[C:17]([CH3:19])=[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: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:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:16](=[O:20])[C:17]([CH3:19])=[CH:18][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH2:33][C:29]1[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=1)[CH:10]=3

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 183583-(Chloromethyl)pyridineHCID 21252859HCID 21252859, compound

Product 1

HCID 19364901HCID 19364901, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

9-bromo-2-hydroxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-one (250 mg) produced in Example 114 was suspended in dimethyl sulfoxide (10 ml), and potassium carbonate (315 mg) was added to the suspension. After stirring at room temperature for 30 minutes, 3-picolylchloride (137 mg) was added to the suspension. After stirring at room temperature for 12 hours, the reaction mixture was poured into ice water (100 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 (250 mg, 78%).

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-1cec9fb5568b4784a60ee75854a07baf
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

Loading…