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

HRID 850775Notes

Reaction equation

HRID 850775 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[C:17]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[C:16](=[O:26])[C:8]4[CH:9]=[C:10]([OH:15])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[C:17]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[C:16](=[O:26])[C:8]4[CH:9]=[C:10]([O:15][CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 1936490510-bromo-2-hydroxy-5-(2-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 1936490310-bromo-2-t-butoxycarbonylmethyloxy-5-(2-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 36.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10-bromo-2-hydroxy-5-(2-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (190 mg) obtained in Example 85 was suspended in dimethyl sulfoxide (10 ml), and potassium carbonate (130 mg) was added. After stirring the mixture at room temperature for 30 minutes, t-butyl bromoacetate (110 mg) was added, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into ice water and extracted with methylene chloride. The methylene chloride layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: methylene chloride containing 3% methanol) to obtain the title compound (88 mg, 36%).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel flash column chromatography (eluent: methylene chloride containing 3% methanol)

Sources & evidence

ORD record
ord-d72b59b89bb04f628f0ee860b98366c8
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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