2,3-Dibromopropene → HCID 86623684, compound

HRID 564052Notes

Reaction equation

HRID 564052 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:22][C:23]([CH2:25]Br)=[CH2:24]>CN(C=O)C.CCOC(C)=O.CO.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:25][C:23]([Br:22])=[CH2:24])[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 105522,3-DibromopropeneHCID 10796Cesium carbonateHCID 36077244-Benzyloxy-2(1H)-pyridone

Product 1

HCID 86623684HCID 86623684, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

To 6.00 g (29.8 mmol) 4-benzyloxy-1H-pyridin-2-one in 30 mL DMF at 0° C. is added 19.4 g (59.6 mmol) cesium carbonate and after 15 min 11.9 g (59.6 mmol) 2,3-dibromo-propene. The reaction mixture is stirred 2 h at RT and is diluted with EtOAc/MeOH and water. The organic phase is washed with water and is dried over MgSO4. After filtration and evaporation of the solvent, the residue is purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Workup

  1. washThe organic phase is washed with water
  2. dry with materialis dried over MgSO4
  3. filtrationAfter filtration and evaporation of the solvent
  4. 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-8dad671cbdc34ca3a5b8234dd2518e1d
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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