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

HRID 73334

反応式

HRID 73334 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-546a537bd389461bb60f96d97b8104a6
出典データセット
uspto-grants-2014_09
特許番号
US08829040B2

関連ノート

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