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

HRID 850774Notes

Reaction equation

HRID 850774 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 water, 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. customThe crystals precipitated
  2. filtrationwere recovered by filtration
  3. washthe resulting crude crystals were washed with a mixed solution of methylene chloride and methanol

Sources & evidence

ORD record
ord-539dd85704224b87980111b8bc5c2aba
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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