Cesium carbonate → 2-{2-[4-(1-Hydroxy-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

HRID 1425758Notes

Reaction equation

HRID 1425758 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10][C:11]2[CH:16]=[N:15][NH:14][C:13](=[O:17])[CH:12]=2)=[N:7][CH:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([CH:34]([OH:36])[CH3:35])=[CH:30][C:29]=1[CH3:37])=[O:27].BrC(Br)=O>CS(C)=O.O>[OH:36][CH:34]([C:31]1[CH:32]=[CH:33][C:28]([C:26](=[O:27])[CH2:25][N:14]2[C:13](=[O:17])[CH:12]=[C:11]([O:10][CH2:9][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][N:7]=3)[CH:16]=[N:15]2)=[C:29]([CH3:37])[CH:30]=1)[CH3:35]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 79057Carbonyl bromideHCID 866955545-(5-Methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-oneHCID 866955582-Bromo-1-[4-(1-hydroxy-ethyl)-2-methyl-phenyl]ethanone

Product 1

HCID 866955592-{2-[4-(1-Hydroxy-ethyl)-2-methyl-phenyl]-2-oxo-ethyl}-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one (preparation 9b, 2.00 g, 8.58 mmol) in DMSO (20 mL) is added cesium carbonate (5.59 g, 17.2 mmol) and the mixture is stirred 10 min at room temperature. Then 2-bromo-1-[4-(1-hydroxy-ethyl)-2-methyl-phenyl]-ethanone (preparation 10b, 2.21 g, 8.58 mmol) is added in portions and the mixture is stirred overnight at room temperature. An additional 0.5 g of the bromoketone is added and the mixture is stirred for 3 h at room temperature. After addition of water, the reaction mixture is extracted with ethyl acetate. The combined organic layer is dried over MgSO4 and evaporated under reduced pressure.

Workup

  1. stirringthe mixture is stirred overnight at room temperature
  2. stirringthe mixture is stirred for 3 h at room temperature
  3. extractionthe reaction mixture is extracted with ethyl acetate
  4. dry with materialThe combined organic layer is dried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b678d557e671473ca6346aa6898a6262
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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