Bromine → HCID 57461001, compound

HRID 1674340Notes

Reaction equation

HRID 1674340 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[N:11]=[C:10]2[CH2:17][CH2:18][CH3:19])[CH:5]=[CH:4][C:3]=1[C:20]1[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=1.C([O-])(=O)C.[Na+].[Br:33]Br>C(O)(=O)C>[Br:33][C:13]1[C:14](=[O:15])[N:9]([CH2:8][C:6]2[CH:5]=[CH:4][C:3]([C:20]3[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=3)=[C:2]([F:1])[CH:7]=2)[C:10]([CH2:17][CH2:18][CH3:19])=[N:11][C:12]=1[CH3:16]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 57461002HCID 57461002, compound

Product 1

HCID 57461001HCID 57461001, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 2′-fluoro-4′-[(4-methyl-6-oxo-2-propylpyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrile (0.78 g), sodium acetate (0.19 g) and acetic acid (10 mL) was added bromine (0.12 mL), and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated from the reaction mixture under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.54 g, 57%).

Workup

  1. customThe solvent was evaporated from the reaction mixture under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe diluted solution was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-535f9fc9852a43f4ae93a108fb75f436
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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