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

HRID 73372

반응식

HRID 73372 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
75 °C

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-61e47699cfcb4f298d9b227daeab03f2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829040B2

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