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

HRID 243762

반응식

HRID 243762 반응식
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

참가 물질

9

반응물 6

HCID 807IodineHCID 7912DiisopropylamineHCID 24477Sodium ThiosulfateHCID 27746352-Fluoro-5-methylpyridineHCID 178418339ButyllithiumHCID 178506721HCID 178506721, 화합물

생성물 1

HCID 102432202-Fluoro-3-iodo-5-methylpyridine수율 33.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d6a7735e45774783b195e275049e73bf
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653277B2

연결된 노트

불러오는 중…