Diisopropylamine → (2,3,4-Trimethoxy-6-methylphenyl)(2-fluoro-4-iodo-5-methyl-3-pyridyl)methanol

HRID 243763

반응식

HRID 243763 반응식
C(NC(C)C)(C)C.FC1C(I)=CC(C)=CN=1.FC1C(I)=C([Li])C(C)=CN=1.[F:27][C:28]1[C:33]([Li])=[C:32]([I:35])[C:31]([CH3:36])=[CH:30][N:29]=1.[CH3:37][O:38][C:39]1[C:46]([O:47][CH3:48])=[C:45]([O:49][CH3:50])[CH:44]=[C:43]([CH3:51])[C:40]=1[CH:41]=[O:42]>O1CCCC1.O.CCCCCC>[CH3:37][O:38][C:39]1[C:46]([O:47][CH3:48])=[C:45]([O:49][CH3:50])[CH:44]=[C:43]([CH3:51])[C:40]=1[CH:41]([C:33]1[C:28]([F:27])=[N:29][CH:30]=[C:31]([CH3:36])[C:32]=1[I:35])[OH:42]

참가 물질

9

반응물 5

HCID 7912DiisopropylamineHCID 896832,3,4-Trimethoxy-6-methylbenzaldehydeHCID 102432202-Fluoro-3-iodo-5-methylpyridineHCID 178506733HCID 178506733, 화합물HCID 178506759HCID 178506759, 화합물

생성물 1

HCID 23082609(2,3,4-Trimethoxy-6-methylphenyl)(2-fluoro-4-iodo-5-methyl-3-pyridyl)methanol수율 75%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

8.90 ml (1.57 mol/l hexane solution) was dropwise added at −78° C. to a solution having 1.34 g (13.3 mmol) of diisopropylamine dissolved in 27 ml of tetrahydrofuran, followed by stirring for 30 minutes. To this solution, a solution having 3.15 g (13.3 mmol) of 2-fluoro-3-iodo-5-methylpyridine obtained in Step (a) dissolved in 5 ml of tetrahydrofuran was added, followed by stirring for 1 hour, so that 2-fluoro-3-iodo-5-methyl-4-pyridyllithium formed at the initial stage was isomerized to 2-fluoro-4-iodo-5-methyl-3-pyridyllithium. To the reaction mixture, a solution having 2.79 g (13.3 mmol) of 2,3,4-trimethoxy-6-methylbenzaldehyde dissolved in 5 ml of tetrahydrofuran was added, followed by stirring for 2 hours. After the temperature was increased to room temperature, 50 ml of water was added, 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 4.45 g (yield: 75%) of (2,3,4-trimethoxy-6-methylphenyl)(2-fluoro-4-iodo-5-methyl-3-pyridyl)methanol.

후처리

  1. additionwas added
  2. customformed at the initial stage
  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-0d388e667ebf463bb8615ceae68a546b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653277B2

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