Dimethylformamide → 4-(4-Fluorobenzyloxy)-1h-pyridin-2-one

HRID 564085Notes

Reaction equation

HRID 564085 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[OH:10][C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(#N)C>[F:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:17][C:15]2[CH:14]=[CH:13][NH:12][C:11](=[O:10])[CH:16]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 178516518HCID 178516518, compound

Product 1

HCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1.40 g (7.41 mmol) 1-bromomethyl-4-fluoro-benzene in 20 mL acetonitrile is added 822 mg (7.40 mmol) 2,4-dihydroxy pyridine and 2.05 g (14.8 mmol) potassium carbonate. The reaction mixture is stirred overnight at RT. 5 mL of DMF is added and the reaction is stirred overnight. After filtration and evaporation of the solvent, is the residue purified by HPLC (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95).

Workup

  1. stirringthe reaction is stirred overnight
  2. filtrationAfter filtration and evaporation of the solvent
  3. custompurified by HPLC (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95)

Sources & evidence

ORD record
ord-e48abbb6b4024a419e6ee356d805565d
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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