Sodium Hydroxide → HCID 19364891, compound

HRID 1530999Notes

Reaction equation

HRID 1530999 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:20])[CH2:18][CH2:19][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH3:16])[CH:10]=3.[CH:21]1[N:26]=[CH:25][N:24]=[CH:23][C:22]=1[CH:27]=O.[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:17](=[O:20])[C:18]([CH2:27][C:22]5[CH:23]=[N:24][CH:25]=[N:26][CH:21]=5)=[CH:19][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH3:16])[CH:10]=3

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2761034Pyrimidine-5-carboxaldehydeHCID 9905551HCID 9905551, compound

Product 1

HCID 19364891HCID 19364891, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

9-bromo-5,6-dihydro-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one (300 mg) obtained in Example 101, step 6 was suspended in ethanol (17 ml), and pyrimidine-5-carboxyaldehyde (157 mg) prepared by the procedure described in Syn. Commun. 24, 253 (1994) and sodium hydroxide (291 mg) dissolved in water (1.7 ml) were added to the suspension at room temperature. The mixture was stirred at room temperature for 12 hours, and approximately half of the solvent was evaporated under reduced pressure. The crystals precipitated were recovered by filtration, and the residue was purified by alumina flash column chromatography (eluent: methylene chloride containing 4% methanol) to obtain the title compound (300 mg, 79%).

Workup

  1. additionwere added to the suspension at room temperature
  2. customapproximately half of the solvent was evaporated under reduced pressure
  3. customThe crystals precipitated
  4. filtrationwere recovered by filtration
  5. customthe residue was purified by alumina flash column chromatography (eluent: methylene chloride containing 4% methanol)

Sources & evidence

ORD record
ord-7a0ad15e84dc45a0a5d3c4166b2d621a
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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