Water → 1-[6-Chloro-1-(3,5-difluoro-benzyl)-1H-indol-3-yl]-2,2,2-trifluoro-ethanone

HRID 1663328ノート

反応式

HRID 1663328 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([F:32])[CH:31]=1)[CH2:27]Br.O>C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])=[CH:7][N:8]2[CH2:27][C:26]2[CH:25]=[C:24]([F:23])[CH:31]=[C:30]([F:32])[CH:29]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5188963,5-Difluorobenzyl bromideHCID 224972521-(6-Chloro-3-indolyl)-2,2,2-trifluoroethanone

生成物 1

HCID 597568221-[6-Chloro-1-(3,5-difluoro-benzyl)-1H-indol-3-yl]-2,2,2-trifluoro-ethanone収率 64%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2.0 g (9.4 mmol) 1-(6-chloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone, 4.59 g (14.1 mmol) cesium carbonate and 2.14 g (10.4 mmol) 3,5-difluorobenzyl bromide in 90 ml acetonitrile was heated at 80° C. for 3 h. After cooling to room temperature addition of 150 ml water was followed by extraction with three 150-ml portions of tert-butyl methyl ether. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated in 30 ml hot cyclohexane. Filtration gave 2.2 g (64%) of the crude title compound as light brown solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionwas followed by extraction with three 150-ml portions of tert-butyl methyl ether
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated in 30 ml hot cyclohexane
  7. filtrationFiltration

出典と根拠

ORDレコード
ord-f3cdbb044aff411e91d089d3b558b875
出典データセット
uspto-grants-2011_10
特許番号
US08034937B2

反応ノート

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