Potassium Carbonate → HCID 67007472, compound

HRID 564139Notes

Reaction equation

HRID 564139 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:22]=[N:23][CH:24]=[CH:25][CH:26]=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:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:3][C:4]2=[O:18])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2459343-(Bromomethyl)pyridineHCID 580427304-Hydroxy-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one

Product 1

HCID 67007472HCID 67007472, compound

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 (2.45 mmol) 3-bromomethyl-pyridine and 0.85 g (6.12 mmol) potassium carbonate. The reaction mixture is stirred overnight at RT, diluted with 60 mL of EtOAc and is washed twice with water. The organic phase is dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Workup

  1. washis washed twice with water
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is evaporated
  5. customThe residue is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90)

Sources & evidence

ORD record
ord-d71256b5b2f84a7caac07326555e23f8
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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