Iodine → 2-Fluoro-3-iodo-5-methylpyridine

HRID 242412

反応式

HRID 242412 の反応式
C([Li])CCC.C(NC(C)C)(C)C.[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=1.FC1C([Li])=CC(C)=CN=1.[I:30]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.O>[F:13][C:14]1[C:19]([I:30])=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=1

参加物

9

反応物 6

HCID 807IodineHCID 7912DiisopropylamineHCID 24477Sodium ThiosulfateHCID 27746352-Fluoro-5-methylpyridineHCID 178418339ButyllithiumHCID 178506721HCID 178506721、化合物

生成物 1

HCID 102432202-Fluoro-3-iodo-5-methylpyridine収率 33.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

26.5 ml of n-butyllithium (1.57 mol/l hexane solution) was dropwise added at −78° C. to a solution having 4.02 g (39.8 mmol) of diisopropylamine dissolved in 70 ml of tetrahydrofuran, followed by stirring for 30 minutes. To this solution, a solution having 4.42 g (39.8 mmol) of 2-fluoro-5-methylpyridine dissolved in 18 ml of tetrahydrofuran was added, followed by stirring for 4 hours to prepare 2-fluoro-5-methyl-3-pyridyllithium. Then, to this solution, a solution having 10.1 g (39.8 mmol) of iodine dissolved in 27 ml of tetrahydrofuran was added, followed by stirring for 2 hours. 16 ml of water and 120 ml of a sodium thiosulfate aqueous solution were charged, followed by extraction with ethyl ether. The organic layer was dried over magnesium sulfate and subjected to filtration, the solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel chromatography to obtain 3.15 g (yield: 33%) of 2-fluoro-3-iodo-5-methylpyridine.

後処理

  1. additionwas added
  2. stirringby stirring for 4 hours
  3. additionwas added
  4. stirringby stirring for 2 hours
  5. extractionfollowed by extraction with ethyl ether
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationsubjected to filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe obtained crude product
  10. customwas purified by silica gel chromatography

出典と根拠

ORDレコード
ord-22aed9edcfd2428bac852decb36eaea7
出典データセット
uspto-grants-2014_02
特許番号
US08653113B2

関連ノート

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