HCID 86649678, 화합물 → ethyl 5-trimethylsilyl-1H-indole-2-carboxylate

HRID 1948785노트

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HRID 1948785 반응식
[N:1]([C:4](=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>C1(C)C=CC=CC=1.FC(F)(F)C(F)(F)C(F)(F)C([O-])=O.[Rh+2].[Rh+2].FC(F)(F)C(F)(F)C(F)(F)C([O-])=O.FC(F)(F)C(F)(F)C(F)(F)C([O-])=O.FC(F)(F)C(F)(F)C(F)(F)C([O-])=O>[CH3:18][Si:17]([CH3:20])([CH3:19])[C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:1][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:10]2

참가 물질

4

반응물 1

HCID 86649678HCID 86649678, 화합물

생성물 1

HCID 66845842ethyl 5-trimethylsilyl-1H-indole-2-carboxylate수율 56.4%

시약·촉매·용매 2

HCID 10942126Rhodium(II) perfluorobutyrate dimer촉매2회HCID 1140Toluene용매

반응 조건

온도
40 °C

실험 절차

0.62 g (0.59 mmol) of the dirhodium(II) heptafluorobutyrate dimer complex is added to a solution of 1.7 g (5.90 mmol) of ethyl 2-azido-3-(3-trimethylsilylphenyl)propenoate prepared according to the procedure described in stage 3.3, in 25 ml of dry toluene, maintained under an inert atmosphere. The reaction mixture is stirred for 7 h at 40° C. A second portion of 0.62 g (0.59 mmol) of the dirhodium(II) heptafluorobutyrate dimer complex is added to the reaction mixture while maintaining the stirring and the heating at 40° C. for a further 1 h. After a return to ambient temperature, the reaction mixture is filtered over silica gel, elution being carried out with toluene. The filtrate is subsequently concentrated under reduced pressure. The greenish solid obtained is triturated several times in a minimum amount of heptane, until a white powder is obtained. The latter is dried under reduced pressure to give 0.87 g of the expected ethyl 5-trimethylsilyl-1H-indole-2-carboxylate in the form of a white powder.

후처리

  1. customprepared
  2. temperaturemaintained under an inert atmosphere
  3. temperaturewhile maintaining the stirring and the heating at 40° C. for a further 1 h
  4. filtrationAfter a return to ambient temperature, the reaction mixture is filtered over silica gel, elution
  5. concentrationThe filtrate is subsequently concentrated under reduced pressure
  6. customThe greenish solid obtained
  7. customis triturated several times in a minimum amount of heptane
  8. customuntil a white powder is obtained
  9. customThe latter is dried under reduced pressure

출처 및 근거

ORD 기록
ord-6b67a9f3f2234696ae48d784f23953ed
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399491B2

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