HCID 19364869, compound → HCID 19364876, compound

HRID 1530959Notes

Reaction equation

HRID 1530959 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-6057dfa2aff24bf19af1795575324592
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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