Bromine → HCID 59469510, compound

HRID 1719086Notes

Reaction equation

HRID 1719086 reaction equation
C([O-])(=O)C.[Na+].[F:6][CH:7]([F:33])[C:8]1[N:9]=[C:10]([CH2:30][CH2:31][CH3:32])[N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)[C:12](=[O:14])[CH:13]=1.[Br:34]Br>C(O)(=O)C>[Br:34][C:13]1[C:12](=[O:14])[N:11]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:20][CH:21]=2)[C:10]([CH2:30][CH2:31][CH3:32])=[N:9][C:8]=1[CH:7]([F:6])[F:33]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 59469455HCID 59469455, compound

Product 1

HCID 59469510HCID 59469510, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of sodium acetate (1 g) and 4′-{[4-(difluoromethyl)-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile (4.4 g) in acetic acid (44 mL) was added bromine (0.62 mL), and the mixture was stirred for 4 hr. Acetic acid was removed in vacuo, and the mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale yellow solid (2.7 g, 61%).

Workup

  1. customAcetic acid was removed in vacuo
  2. additionthe mixture was diluted with ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ef3a496039044db78955c181c408ecc8
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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