Acetic Acid → HCID 22562008, 화합물

HRID 983020노트

반응식

HRID 983020 반응식
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.C([OH:24])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]>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][C:10](=[O:24])[NH:11]2

참가 물질

7

반응물 4

HCID 176Acetic Acid2회HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 22561889HCID 22561889, 화합물

생성물 1

HCID 22562008HCID 22562008, 화합물수율 74%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 6386tert-Butanol용매

실험 절차

To the suspension of 4-biphenyl-2-yl-1H-indole (1.18 g, 4.4 mmol) in t-BuOH: ethanol: acetic acid (28 mL: 17 mL: 9 mL) was added pyridinium tribromide (4.39 g, 13.7 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added acetic acid (22 mL). Zinc dust (1.63 g, 25 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 (3×), sat. NaHCO3, brine, dried over Na2SO4, concentrated and triturated with ether to give 0.93 g (74%) of 4-biphenyl-2-yl-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 (3×), sat. NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customtriturated with ether

출처 및 근거

ORD 기록
ord-ada545fe62144c948652dae6add3c06f
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06861418B2

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