Cesium carbonate → 5-Benzyloxy-2-[2-(4-hydroxymethyl-phenyl)-ethyl]-2H-pyridazin-3-one

HRID 564165Notes

Reaction equation

HRID 564165 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[N:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][OH:32])=[CH:27][CH:26]=1>CN(C=O)C.CCOC(C)=O.CO.O>[CH2:1]([O:8][C:9]1[CH:14]=[N:13][N:12]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][OH:32])=[CH:27][CH:26]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 53929068[4-(2-Chloroethyl)phenyl]methanolHCID 598221075-(benzyloxy)pyridazin-3(2H)-one

Product 1

HCID 670075955-Benzyloxy-2-[2-(4-hydroxymethyl-phenyl)-ethyl]-2H-pyridazin-3-one

Reagents, catalysts & solvents 4

HCID 887MethanolCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 200 mg (0.99 mmol) 5-benzyloxy-2H-pyridazin-3-one (preparation 5) in 1.0 mL DMF is added 645 mg (1.98 mmol) cesium carbonate and the mixture is stirred 15 min at RT. Then 518 mg (1.98 mmol) [4-(2-iodo-ethyl)-phenyl]-methanol (preparation 1b) is added and the reaction mixture is stirred overnight. The mixture is diluted with EtOAc, a few drops of MeOH and water. The layers are separated, the organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated. The precipitate is elutriated in acetone and the product is collected by filtration and dried.

Workup

  1. stirringthe reaction mixture is stirred overnight
  2. customThe layers are separated
  3. washthe organic phase is washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. filtrationthe product is collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-7b6021866e3a484391490aa4313cb5a8
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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