Acetic Acid → 4-(3-Trifluoromethyl-phenyl)-1,3-dihydro-indol-2-one

HRID 1839612

반응식

HRID 1839612 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][NH:13]3)[CH:6]=[CH:7][CH:8]=1.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(O)(=[O:43])C>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][C:12](=[O:43])[NH:13]3)[CH:6]=[CH:7][CH:8]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 21124087PyridiniumtribromideHCID 225616744-(3-Trifluoromethyl-phenyl)-1H-indole

생성물 1

HCID 225619054-(3-Trifluoromethyl-phenyl)-1,3-dihydro-indol-2-one수율 58%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 86587657t-BuOH ethanol aceticacid용매

반응 조건

온도
27 °C

실험 절차

To the suspension of 4-(3-trifluoromethyl-phenyl)-1H-indole (3.37 g, 12.90 mmol) in t-BuOH-ethanol-acetic acid (3:2:1) (155 mL) was added pyridinium tribromide (12.38 g, 38.70 mmol)) portionwise. The mixture was stirred at 27° C. for 3 hours, and then to the mixture was added acetic acid (63 mL). Zinc dust was added to the reaction mixture portionwise until the color changed from deep red to light yellow, and the reaction mixture was stirred at room temperature for one hour. The unreacted zinc dust was filtered off and washed with ethanol. The filtrate was concentrated, and the syrupy residue was dissolved in ethyl acetate, which was washed with water, 0.5 N HCl, sat. NaHCO3 and brine, and dried over Na2SO4. After filtration and evaporation, the crude product was triturated with diethyl ether to provide product 4-(3-trifluoromethyl-phenyl)-1,3-dihydro-indol-2-one (2.07 g, 58%) as a tan solid.

후처리

  1. stirringwas stirred at room temperature for one hour
  2. filtrationThe unreacted zinc dust was filtered off
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe syrupy residue was dissolved in ethyl acetate
  6. washwhich was washed with water, 0.5 N HCl, sat. NaHCO3 and brine
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration and evaporation
  9. customthe crude product was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-18ea81048fe04d52b297f060d1e1b418
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677368B2

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