Ammonia → 4-[6,7-dimethoxy-2-(4-pyridyl)methylphthalazin-1(2H)-on-4-yl]-2-[4-(3-pyridyl)-phthalazin-1(2H)-on-2-yl]pyridine

HRID 1739415Notes

Reaction equation

HRID 1739415 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][N:8]=2)[CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:25]1[CH:30]=[C:29]([C:31]2[C:40]3[C:35](=[CH:36][C:37]([O:43][CH3:44])=[C:38]([O:41][CH3:42])[CH:39]=3)[C:34](=[O:45])[N:33]([CH2:46][C:47]3[CH:52]=[CH:51][N:50]=[CH:49][CH:48]=3)[N:32]=2)[CH:28]=[CH:27][N:26]=1.N>CN(C)C=O.[Cu](I)I>[CH3:42][O:41][C:38]1[CH:39]=[C:40]2[C:35](=[CH:36][C:37]=1[O:43][CH3:44])[C:34](=[O:45])[N:33]([CH2:46][C:47]1[CH:48]=[CH:49][N:50]=[CH:51][CH:52]=1)[N:32]=[C:31]2[C:29]1[CH:30]=[CH:25][N:26]=[C:27]([N:9]2[N:8]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:17])[CH:28]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 100138394-(3-pyridyl)phthalazin-1(2H)-oneHCID 158702972-bromo-4-[6,7-dimethoxy-2-(4-pyridyl)methyl-phthalazin-1(2H)-on-4-yl]pyridine

Product 1

HCID 158702984-[6,7-dimethoxy-2-(4-pyridyl)methylphthalazin-1(2H)-on-4-yl]-2-[4-(3-pyridyl)-phthalazin-1(2H)-on-2-yl]pyridineYield 49.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3-pyridyl)phthalazin-1(2H)-one (167 mg) in dimethylformamide (5 ml) are added successively potassium carbonate (103 mg), copper iodide (70 mg) and 2-bromo-4-[6,7-dimethoxy-2-(4-pyridyl)methyl-phthalazin-1(2H)-on-4-yl]pyridine (335 mg) under nitrogen atmosphere, and the mixture is refluxed for two hours. The reaction mixture is cooled, and thereto is added aqueous ammonia. The mixture is extracted with chloroform, and the extract is washed, dried, concentrated, and purified by silica gel column chromatography (solvent; chloroform:methanol=19:1) to give 4-[6,7-dimethoxy-2-(4-pyridyl)methylphthalazin-1(2H)-on-4-yl]-2-[4-(3-pyridyl)-phthalazin-1(2H)-on-2-yl]pyridine (216 mg).

Workup

  1. temperaturethe mixture is refluxed for two hours
  2. temperatureThe reaction mixture is cooled
  3. extractionThe mixture is extracted with chloroform
  4. washthe extract is washed
  5. customdried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (solvent; chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-bbe7a6684269477ba19df4aeae294781
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

Loading…