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

HRID 1371848

반응식

HRID 1371848 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 7237O-Xylene용매HCID 25517Ammonium Chloride용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-463b9612b6b44288b2f7c6f4e2f531bb
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157488B2

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