Cesium carbonate → 1-[2-(4-Hydroxymethyl-phenyl)-ethyl]-4-phenethyl-1H-pyridin-2-one

HRID 564158Notes

Reaction equation

HRID 564158 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[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.O.CO>[OH:32][CH2:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH2:23][N:12]2[CH:13]=[CH:14][C:9]([CH2:1][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:10][C:11]2=[O:15])=[CH:26][CH:27]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 2680294-(2-Phenylethyl)pyridin-2(1h)-oneHCID 18402547[4-(2-Iodo-ethyl)-phenyl]-methanol

Product 1

HCID 670073171-[2-(4-Hydroxymethyl-phenyl)-ethyl]-4-phenethyl-1H-pyridin-2-one

Reagents, catalysts & solvents 4

HCID 887MethanolCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 200 mg (1.01 mmol) 4-phenethyl-1H-pyridin-2-one in 1.0 mL DMF is added at 0° C. 650 mg (2.01 mmol) cesium carbonate and the mixture is stirred 15 min at 0° C. Then 0.53 g (2.01 mmol) [4-(2-iodo-ethyl)-phenyl]-methanol (preparation 1b) is added, the mixture is warmed to RT and is stirred overnight at RT. The reaction mixture is diluted with EtOAc, water and a few drops of MeOH, the layers are separated and the organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated. The residue is dissolved in MeOH/DMF and is purified via HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Workup

  1. customthe layers are separated
  2. washthe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. dissolutionThe residue is dissolved in MeOH/DMF
  7. customis purified via HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90)

Sources & evidence

ORD record
ord-d8192c0675c34e4f95759f7bff0b4e78
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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