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

HRID 1530979Notes

Reaction equation

HRID 1530979 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:19]=[C:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[C:17](=[O:27])[C:8]4[CH:9]=[C:10]([O:15]C)[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:19]=[C:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[C:17](=[O:27])[C:8]4[CH:9]=[C:10]([OH:15])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 1936490010-bromo-2-methoxy-5-(2-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 1936490510-bromo-2-hydroxy-5-(2-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10-bromo-2-methoxy-5-(2-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one (0.54 g) obtained in Example 84 was suspended in anhydrous methylene chloride (30 ml), and boron tribromide (5 ml) was added dropwise at room temperature. The mixture was stirred at room temperature for 12 hours, and the reaction mixture was poured into ice wacer, and to this mixture was added saturated aqueous solution of sodium carbonate until the termination of foaming. The crystals precipitated were recovered by filtration, and the resulting crude crystals were washed with a mixed solution of methylene chloride and methanol to obtain the title compound (0.173 g, 33%).

Workup

  1. additionthe reaction mixture was poured into ice wacer
  2. customThe crystals precipitated
  3. filtrationwere recovered by filtration
  4. washthe resulting crude crystals were washed with a mixed solution of methylene chloride and methanol

Sources & evidence

ORD record
ord-5a13a91d854040799de43ebd47b15918
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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