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

HRID 983014

反応式

HRID 983014 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 86587657t-BuOH ethanol aceticacid溶媒

反応条件

温度
27 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9ab1bec94b2c411d98cfe53e53edfd7d
出典データセット
uspto-grants-2005_03
特許番号
US06861418B2

関連ノート

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