1,10-Phenanthroline → 1-Phenyl-1H-indole-6-carbaldehyde

HRID 1666791

反応式

HRID 1666791 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.N1[C:25]2[C:16](=[CH:17][CH:18]=[C:19]3[C:24]=2N=CC=C3)C=CC=1.C(=CC(/C=C/C1C=CC=CC=1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].IC1C=CC=CC=1>C1(C)C(C)=CC=CC=1.ClCCl.[Cl-].[NH4+]>[C:16]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=3)[CH:3]=[CH:2]2)[CH:25]=[CH:24][CH:19]=[CH:18][CH:17]=1

参加物

9

反応物 5

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 27734351H-Indole-6-carboxaldehydeHCID 5354370trans-Dibenzylideneacetone

生成物 1

HCID 210713941-Phenyl-1H-indole-6-carbaldehyde

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 7237O-Xylene溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
110 °C

実験手順

Combine in a sealed tube 1H-indole-6-carbaldehyde 0.9 g, 6.2 mmol), copper(I) trifluoromethanesulfate-complex (0.2 g, 0.3 mmol), phenanthroline (1.3 g, 6.2 mmol), transdibenzylidenacetone (0.1 g, 0.3 mmol), cesium carbonate (2.6 g, 7.9 mmol) and iodobenzene (1.6 ml, 14.3 mmol) in xylene (40 ml). Heat at about 110° C. After 24 hours, cool to room temperature, dilute with dichloromethane and saturated ammonium chloride. Separate the layer and Extract the aqueous layer with dichloromethane. Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrated to give a residue. Chromatograph the residue eluting with 8:2 hexane:EtOAc to give the title compound.

後処理

  1. temperaturecool to room temperature
  2. customSeparate the layer
  3. extractionExtract the aqueous layer with dichloromethane
  4. washwash sequentially with distilled water and brine
  5. dry with materialdry (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrated
  8. customto give a residue
  9. washChromatograph the residue eluting with 8:2 hexane

出典と根拠

ORDレコード
ord-8c35c81f2248442d9041f4460566c6d8
出典データセット
uspto-grants-2011_10
特許番号
US08044090B2

関連ノート

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