Potassium Iodide → 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine

HRID 71179ノート

反応式

HRID 71179 の反応式
[Br:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([NH:10][CH:11]=O)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].ClC[C:23](=O)[CH3:24].[CH3:26][N:27](C=O)C>>[Br:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N:10]2[CH:11]=[C:23]([CH3:24])[N:27]=[CH:26]2)=[CH:4][CH:3]=1

参加物

6

反応物 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 6571ChloroacetoneHCID 10796Cesium carbonateHCID 71492501N-(6-bromo-2-methoxypyridin-3-yl)formamide

生成物 1

HCID 576093006-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine

実験手順

To a mixture of N-(6-bromo-2-methoxypyridin-3-yl)formamide (8.0 g), cesium carbonate (20.1 g) and potassium iodide (580 mg) in DMF (40 mL) was added 1-chloropropan-2-one (4.13 mL), and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Acetic acid (50 mL) and ammonium acetate (26.7 g) were added to the residue, and the mixture was stirred at 130° C. for 3 hr. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. Water was added, and the mixture was neutralized with aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.72 g).

後処理

  1. customThe solvent was evaporated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. additionAcetic acid (50 mL) and ammonium acetate (26.7 g) were added to the residue
  8. stirringthe mixture was stirred at 130° C. for 3 hr
  9. temperatureto cool to room temperature
  10. customthe solvent was evaporated under reduced pressure
  11. additionWater was added
  12. extractionextracted with ethyl acetate
  13. dry with materialThe extract was dried over anhydrous magnesium sulfate
  14. customthe solvent was evaporated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-c199a4d668fb4c39a80174b93f5a2aff
出典データセット
uspto-grants-2014_09
特許番号
US08822699B2

反応ノート

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