Dimethylformamide → HCID 67006610, compound

HRID 564124Notes

Reaction equation

HRID 564124 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][C:24]([F:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(#N)C.CCOC(C)=O>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:1][C:2]2[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=3)[C:4](=[O:18])[CH:3]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 580427304-Hydroxy-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one

Product 1

HCID 67006610HCID 67006610, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 400 mg (1.63 mmol) 4-hydroxy-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one (preparation 2b) in 30 mL acetonitrile is added 0.22 mL (1.79 mmol) 1-bromomethyl-4-fluoro-benzene and 0.45 g (3.26 mmol) potassium carbonate. The reaction mixture is stirred overnight at RT. 5.0 mL DMF is added and the reaction mixture is stirred additional 24 h at RT. The reaction mixture is 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 (Waters symmetry C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Workup

  1. stirringthe reaction mixture is stirred additional 24 h at RT
  2. washis washed twice with water
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customThe residue is purified via reverse HPLC chromatography (Waters symmetry C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90)

Sources & evidence

ORD record
ord-220d0b80ccc0408faba1fe386a24be72
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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