Sodium Iodide → 3-(2-Cyanophenyl)-5-(2-pyridyl)-2(1H)-pyridone

HRID 229657Notes

Reaction equation

HRID 229657 reaction equation
Cl[Si](C)(C)C.[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[C:15]([O:26]C)=[N:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:19]=1)#[N:7].[I-].[Na+].C(=O)(O)[O-].[Na+]>C(#N)C>[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[C:15](=[O:26])[NH:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:19]=1)#[N:7]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 223190893-(2-Cyanophenyl)-5-(2-pyridyl)-2-methoxypyridine

Product 1

HCID 223189453-(2-Cyanophenyl)-5-(2-pyridyl)-2(1H)-pyridoneYield 57.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Chlorotrimethylsilane (0.1 ml) was added to a suspension of 0.20 g of 3-(2-cyanophenyl)-5-(2-pyridyl)-2-methoxypyridine and 0.12 g of sodium iodide in 10 ml of acetonitrile and the mixture was stirred at room temperature for 3 hours. A saturated sodium bicarbonate solution was added to the mixture followed by extracting with ethyl acetate. The ethyl acetate layer was washed with water and a saturated saline solution and dried over magnesium sulfate. The solvent was concentrated in vacuo and the residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:1) to give 0.11 g of the title compound in pale yellow powder.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materiala saturated saline solution and dried over magnesium sulfate
  4. concentrationThe solvent was concentrated in vacuo
  5. customthe residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-c1166e3b660d48e5b6f263e265c9facd
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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