Potassium Carbonate → 1-[2-(4-hydroxymethylphenyl)-ethyl]-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one

HRID 564108Notes

Reaction equation

HRID 564108 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=2)[C:4](=[O:18])[CH:3]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[OH:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][N:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:3][C:4]2=[O:18])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5642092-(Bromomethyl)pyridineHCID 580427304-Hydroxy-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one

Product 1

HCID 670066931-[2-(4-hydroxymethylphenyl)-ethyl]-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 500 mg (2.04 mmol) 4-hydroxy-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one (preparation 2b) in 20 mL DMF is added 0.62 g (2.46 mmol) 2-bromomethyl-pyridine and 0.85 g (6.12 mmol) potassium carbonate. The reaction mixture is stirred overnight at RT and is diluted with 60 mL of EtOAc. The organic phase is washed twice with water, separated, dried over MgSO4 and the solvent is evaporated to afford the product.

Workup

  1. washThe organic phase is washed twice with water
  2. customseparated
  3. dry with materialdried over MgSO4
  4. customthe solvent is evaporated
  5. customto afford the product

Sources & evidence

ORD record
ord-c7544adc4bac4dd4af4494cc36499ce4
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

Loading…