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

HRID 1911249노트

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HRID 1911249 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

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 the preceding step, in 25 mL of dry toluene, maintained under an inert atmosphere, is added 0.62 g (0.59 mmol) of dirhodium (II) heptafluorobutyrate dimer complex. The reaction mixture is stirred for 7 hours at 40° C. A second portion of 0.62 g (0.59 mmol) of dirhodium (II) heptafluorobutyrate dimer complex is added to the reaction mixture while maintaining the stirring and heating at 40° C. for a further 1 hour. After cooling to room temperature, the reaction mixture is filtered through silica gel, eluting with toluene. The filtrate is then concentrated under reduced pressure. The greenish solid obtained is triturated several times in a minimum amount of heptane, until a white powder is obtained. This powder 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. temperaturemaintained under an inert atmosphere
  2. temperaturewhile maintaining the stirring and
  3. temperatureheating at 40° C. for a further 1 hour
  4. temperatureAfter cooling to room temperature
  5. filtrationthe reaction mixture is filtered through silica gel
  6. washeluting with toluene
  7. concentrationThe filtrate is then concentrated under reduced pressure
  8. customThe greenish solid obtained
  9. customis triturated several times in a minimum amount of heptane
  10. customuntil a white powder is obtained
  11. customThis powder is dried under reduced pressure

출처 및 근거

ORD 기록
ord-e5d7f90fd0d644cbb7a2ca288a869d98
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604050B2

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