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

HRID 1839603노트

반응식

HRID 1839603 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[CH:11][NH:12]3)=[CH:4][CH:3]=1.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(O)(=[O:40])C>CC(O)(C)C.C(O)C.C(O)(=O)C.[Zn]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][C:11](=[O:40])[NH:12]3)=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 21124087PyridiniumtribromideHCID 225616864-(4-fluorophenyl)-1H-indole

생성물 1

HCID 225618524-(4-Fluoro-phenyl)-1,3-dihydro-indol-2-one수율 98%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 86587657t-BuOH ethanol aceticacid용매

반응 조건

온도
27 °C

실험 절차

To the suspension of 4-(4-fluoro-phenyl)-1H-indole (2.28 g, 10.79 mmol) in t-BuOH-ethanol-acetic acid (3:2:1) (147 mL) was added pyridinium tribromide (90% purity from Aldrich, 11.51 g, 32.38 mmol)) portionwise. The mixture was stirred at 27° C. for 3 hours, and then to the mixture was added acetic acid (108 mL). Zinc dust (10.52 g, 162 mmol) was added to the reaction mixture portionwise, 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 suspended in water for 4 hour. The solid product was precipitated out, filtered, and washed repeatedly with water to remove the zinc salt and pyridine salt. After high vacuum dry, a pure product (2.40 g, 98%) was obtained.

후처리

  1. stirringthe reaction mixture was 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. waitthe syrupy residue was suspended in water for 4 hour
  6. customThe solid product was precipitated out
  7. filtrationfiltered
  8. washwashed repeatedly with water
  9. customto remove the zinc salt and pyridine salt
  10. customAfter high vacuum dry

출처 및 근거

ORD 기록
ord-76556d42b5f64c71a6321a76741582a9
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677368B2

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