Chlorotrimethylsilane → 1-(1-Methyl-1H-indol-3-yl)-3-(4-pyridyl)-3-trimethylsilyloxypropan-1-one

HRID 362792노트

반응식

HRID 362792 반응식
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH3:25])[CH:17]=1)(=[O:15])[CH3:14].[N:26]1[CH:31]=[CH:30][C:29]([CH:32]=[O:33])=[CH:28][CH:27]=1.Cl[Si:35]([CH3:38])([CH3:37])[CH3:36]>C1COCC1>[CH3:25][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([C:13](=[O:15])[CH2:14][CH:32]([C:29]2[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=2)[O:33][Si:35]([CH3:38])([CH3:37])[CH3:36])=[CH:17]1

참가 물질

7

반응물 5

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 133894-PyridinecarboxaldehydeHCID 5941561-(1-Methyl-1H-indol-3-yl)ethanoneHCID 178418339Butyllithium

생성물 1

HCID 232995901-(1-Methyl-1H-indol-3-yl)-3-(4-pyridyl)-3-trimethylsilyloxypropan-1-one수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

1.6M n-Butyllithium (1.19 ml, 1.90 mmol) was added to dry THF (10 ml) containing diisopropylamine (0.266 ml, 1.90 mmol) under Ar at 0° C. After 15 mins, the mixture was cooled to -78° C., and 3-acetyl-1-methyl-1H-indole (0.300 g, 1.73 mmol) in dry THF (5 ml) was added slowly. The resulting mixture was left at -78° C. for 1 h, before pyridine-4-carboxaldehyde (0.165 ml, 1.73 mmol) was added. The reaction mixture was then left at -78° C. for 1 h, before being allowed to warm to 0° C., whereupon chlorotrimethylsilane (0.439 ml, 3.46 mmol) was added. The mixture was then allowed to warm to room temp and stirred for 1 h, before being evaporated under reduced pressure and partitioned between dichloromethane and water. The organic layer was then dried (Na2SO4) and evaporated under reduced pressure to give a pale yellow solid which was purified by silica-gel chromatography (EtOAc as eluant) to give the title compound as a yellow solid (0.300 g, 51%).

후처리

  1. additionwas added
  2. waitThe reaction mixture was then left at -78° C. for 1 h
  3. additionwas added
  4. temperatureto warm to room temp
  5. custombefore being evaporated under reduced pressure
  6. custompartitioned between dichloromethane and water
  7. dry with materialThe organic layer was then dried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customto give a pale yellow solid which
  10. customwas purified by silica-gel chromatography (EtOAc as eluant)

출처 및 근거

ORD 기록
ord-9b76f0a879d646e1a4ec574363aec2e4
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05872134

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