Dimethylformamide → 2-bromo-4-[6,7-dimethoxy-2-(4-pyridyl)methyl-phthalazin-1(2H)-on-4-yl]pyridine

HRID 1739426Notes

Reaction equation

HRID 1739426 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[C:11](=[O:22])[NH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.Cl.[N:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[C:11](=[O:22])[N:10]([CH2:30][C:27]3[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 218408052-bromo-4-(6,7-dimethoxyphthalazin-1(2H)-on-4-yl)pyridine

Product 1

HCID 158702972-bromo-4-[6,7-dimethoxy-2-(4-pyridyl)methyl-phthalazin-1(2H)-on-4-yl]pyridineYield 78.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-4-(6,7-dimethoxyphthalazin-1(2H)-on-4-yl)pyridine (362 mg), 4-picolyl chloride hydrochloride (180 mg), and potassium carbonate (359 mg) are added to dimethylformamide (10 ml), and the mixture is heated with stirring at 80° C. for three hours under nitrogen atmosphere. Water is added to the reaction mixture, and the mixture is extracted with methylene chloride. The extract is washed, dried, and concentrated to give 2-bromo-4-[6,7-dimethoxy-2-(4-pyridyl)methylphthalazin-1(2H)-on-4-yl]pyridine (355 mg).

Workup

  1. temperaturethe mixture is heated
  2. extractionthe mixture is extracted with methylene chloride
  3. washThe extract is washed
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1ee5755ca0934618bb07b1e373123573
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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