Acetic Acid → HCID 22561714, 화합물

HRID 983033노트

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HRID 983033 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2.C([OH:20])C.C(O)(=O)C.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CC(O)(C)C.[Zn]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][C:12](=[O:20])[NH:13]2

참가 물질

7

반응물 4

HCID 176Acetic Acid2회HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 22561815HCID 22561815, 화합물

생성물 1

HCID 22561714HCID 22561714, 화합물수율 75%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 6386tert-Butanol용매

실험 절차

To the suspension of 4-(2,4-difluoro-phenyl)-1H-indole (6.42 g, 28 mmol) in t-BuOH: ethanol: acetic acid (177 mL: 105 mL: 55 mL) was added pyridinium tribromide (27 g, 84 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added with acetic acid (136 mL). Zinc dust (9.8 g, 150 mmol) was added to the reaction mixture portionwise. After stirring for one hour, any unreacted zinc was filtered off and most of the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate, washed with water (5×), neutralized with 1N HCl, washed with sat. NaHCO3, brine, dried over Na2SO4, concentrated and triturated with ether to give 5.16 g (75%) of 4-(2,4-difluoro-phenyl) 1,3-dihydro-indol-2-one.

후처리

  1. stirringAfter stirring for one hour
  2. filtrationany unreacted zinc was filtered off and most of the solvent
  3. customwas removed under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water (5×)
  6. washwashed with sat. NaHCO3, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customtriturated with ether

출처 및 근거

ORD 기록
ord-d95acc4deb5648e7b030f382ed5fc331
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06861418B2

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