Water → HCID 18412008, compound

HRID 992265Notes

Reaction equation

HRID 992265 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][OH:10])[CH:4]=1.Br[C:12]1[C:13](=[O:32])[N:14]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[N:15]=[C:16]([C:19]2([CH3:24])[O:23][CH2:22][CH2:21][O:20]2)[C:17]=1[CH3:18].O>CN(C)C=O>[F:31][C:28]1[CH:27]=[CH:26][C:25]([N:14]2[C:13](=[O:32])[C:12]([O:10][CH2:9][C:5]3[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=3)=[C:17]([CH3:18])[C:16]([C:19]3([CH3:24])[O:23][CH2:22][CH2:21][O:20]3)=[N:15]2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 75103-PyridinemethanolHCID 24758Sodium hydrideHCID 18412020HCID 18412020, compound

Product 1

HCID 18412008HCID 18412008, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 62.5% sodium hydride (92 mg) in N,N-dimethylformamide (8 ml) was added 3-pyridylcarbinol (0.25 ml) under ice cooling, followed by stirring at room temperature for 20 minutes. Then, 4-bromo-2-(4-fluorophenyl)-5-methyl-6-(2-methyl-1,3-dioxolan-2-yl)-3(2H)-pyridazinone (738 mg) was added, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After washing with water and a brine, the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, and the resulting residue was crystallized from ether to obtain 2-(4-fluorophenyl)-5-methyl-6-(2-methyl-1,3-dioxolan-2-yl)-4-(3-pyridylmethoxy)-3(2H)-pyridazinone (320 mg).

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washAfter washing with water
  4. dry with materiala brine, the organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation
  6. customthe resulting residue was crystallized from ether

Sources & evidence

ORD record
ord-8fc7dfb2e0f74442b46a1233740f67ab
Source dataset
uspto-grants-2002_10
Patent number
US06469003B1

Reaction notes

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