Ethyl Acetate → 3-(3-Cyanoindol-1-yl)benzoic acid ethyl ester

HRID 73372

反応式

HRID 73372 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]#[N:11])=[CH:2]1.[CH2:12]([O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18](I)[CH:17]=1)[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CS(C)=O.[Cu](I)I>[CH2:12]([O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]#[N:11])=[CH:2]2)[CH:17]=1)[CH3:13]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 143542Ethyl 3-iodobenzoateHCID 2302823-Cyanoindole

生成物 1

HCID 584374173-(3-Cyanoindol-1-yl)benzoic acid ethyl ester収率 66.5%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
75 °C

実験手順

To a solution of 1H-indole-3-carbonitrile (0.28 g) in dimethyl sulfoxide (3 mL) were added 3-iodobenzoic acid ethyl ester (0.61 g), cesium carbonate (0.65 g), copper iodide (0.038 g) and N,N-dimethyl grycine (0.041 g), this mixture was stirred at 75° C. for 3 days. To this reaction mixture was added ethyl acetate, the insoluble material was removed by filtration and this filtrate was concentrated under reduced pressure. To this residue was added water, the precipitated solid was collected by filtration, and washed with water and n-hexane, and dried under reduced pressure at 40° C. to give the title compound (0.38 g).

後処理

  1. customthe insoluble material was removed by filtration
  2. concentrationthis filtrate was concentrated under reduced pressure
  3. additionTo this residue was added water
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with water and n-hexane
  6. customdried under reduced pressure at 40° C.

出典と根拠

ORDレコード
ord-61e47699cfcb4f298d9b227daeab03f2
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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