Water → 1-(5-Formylfuran-2-yl)-1H-indole-3-carbonitrile

HRID 73334

반응식

HRID 73334 반응식
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)#[N:2].Br[C:13]1[O:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH:18]([C:16]1[O:17][C:13]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]([C:1]#[N:2])=[CH:4]2)=[CH:14][CH:15]=1)=[O:19]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2302823-CyanoindoleHCID 6003285-Bromofuran-2-carbaldehyde

생성물 1

HCID 584373031-(5-Formylfuran-2-yl)-1H-indole-3-carbonitrile수율 37%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A suspension of 3-cyanoindole (0.14 g), 5-bromo-2-furaldehyde (0.18 g), and cesium carbonate (0.39 g) in N,N-dimethylformamide (3 mL) was stirred at room temperature or 3 hours. This reaction mixture was heated at 50° C., stirred for 2 hours. After cooling to ambient, water was added to this reaction mixture. This mixture was extracted with ethyl acetate, and this organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate-2/1) to give the title compound (0.086 g).

후처리

  1. temperatureThis reaction mixture was heated at 50° C.
  2. stirringstirred for 2 hours
  3. additionwas added to this reaction mixture
  4. extractionThis mixture was extracted with ethyl acetate
  5. washthis organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate-2/1)

출처 및 근거

ORD 기록
ord-546a537bd389461bb60f96d97b8104a6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829040B2

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