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

HRID 1530983Notes

Reaction equation

HRID 1530983 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:17](=[O:27])[C:18]([CH2:20][C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)=[CH:19][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15]C)[CH:10]=3.B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:17](=[O:27])[C:18]([CH2:20][C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)=[CH:19][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([OH:15])[CH:10]=3

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 193648679-bromo-2-methoxy-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 212528709-bromo-2-hydroxy-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-oneYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

9-bromo-2-methoxy-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one (700 mg) obtained in Example 101 was suspended in anhydrous methylene chloride (70 ml), and to the suspension was added dropwise a solution of boron tribromide in methylene chloride (1M; 10 ml) at room temperature. The reaction mixture was stirred at room temperature for 12 hours, and poured into ice water (100 ml). To this mixture was added saturated aqueous solution of sodium carbonate until the termination of foaming. The crystals precipitated were recovered by filtration. The thus obtained crude crystals were washed with ethanol and ether in succession to obtain the title compound (450 mg, 67%).

Workup

  1. customThe crystals precipitated
  2. filtrationwere recovered by filtration
  3. customThe thus obtained crude crystals
  4. washwere washed with ethanol and ether in succession

Sources & evidence

ORD record
ord-869f1f6d29bf401b81cc4fbe56d9272b
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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