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

HRID 1530978Notes

Reaction equation

HRID 1530978 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH2:19][CH2:18][C:17](=[O:20])[C:8]4[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]=O.[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:19]=[C:18]([CH2:27][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=4)[C:17](=[O:20])[C:8]4[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

6

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 988395610-bromo-5,6-dihydro-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 1936490010-bromo-2-methoxy-5-(2-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

10-bromo-5,6-dihydro-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one (0.7 g) obtained in Example 1, step 3 was suspended in ethanol (30 ml), and pyridine-2-aldehyde (0.7 g) and sodium hydroxide (0.3 g) dissolved in water (5 ml) were added at room temperature. The mixture was stirred at room temperature for 12 hours, and approximately half of the solvent was evaporated under reduced pressure. The precipitated crystals were recovered by filtration, and washed with water, ethanol and ether in succession to obtain the title compound (0.56 g, 61%).

Workup

  1. additionwere added at room temperature
  2. customapproximately half of the solvent was evaporated under reduced pressure
  3. filtrationThe precipitated crystals were recovered by filtration
  4. washwashed with water, ethanol and ether in succession

Sources & evidence

ORD record
ord-3163196fe259401497858f1930d3422b
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

Loading…