Acetic Acid → HCID 22561714、化合物

HRID 1839631ノート

反応式

HRID 1839631 の反応式
[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

参加物

7

反応物 4

HCID 176Acetic Acid2 回HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 22561815HCID 22561815、化合物

生成物 1

HCID 22561714HCID 22561714、化合物収率 75%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 6386tert-Butanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4cede0908bc046339fe554341a4e091e
出典データセット
uspto-grants-2004_01
特許番号
US06677368B2

反応ノート

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