HCID 19364869, compound → HCID 19364876, compound

HRID 850751Notes

Reaction equation

HRID 850751 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:24]=[C:23]([CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[C:22](=[O:32])[C:8]4[CH:9]=[C:10]([O:15][CH2:16][C:17](=[O:21])[CH2:18][CH2:19][CH3:20])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.B.[Na]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:24]=[C:23]([CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[C:22](=[O:32])[C:8]4[CH:9]=[C:10]([O:15][CH2:16][CH:17]([OH:21])[CH2:18][CH2:19][CH3:20])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

4

Reactant 2

HCID 19364869HCID 19364869, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 19364876HCID 19364876, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10-bromo-2-(2-oxopentyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (400 mg) obtained in Example 40 was suspended in anhydrous methanol (20 ml), and to the suspension was added in small portions sodium boron hydride (92 mg) in an ice bath, and the mixture was stirred at room temperature for 12 hours. The solvent was evaporated under reduced pressure and the residue was extracted by adding water and 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 4% methanol) to obtain the title compound (140 mg; 28%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted
  3. additionby adding water and methylene chloride
  4. washThe methylene chloride layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel flash column chromatography (eluent: methylene chloride containing 4% methanol)

Sources & evidence

ORD record
ord-0c109d0dcf7f416f91de581a48880e3c
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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