HCID 86649678、化合物 → ethyl 5-trimethylsilyl-1H-indole-2-carboxylate

HRID 1948785ノート

反応式

HRID 1948785 の反応式
[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

参加物

4

反応物 1

HCID 86649678HCID 86649678、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 10942126Rhodium(II) perfluorobutyrate dimer触媒2 回HCID 1140Toluene溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6b67a9f3f2234696ae48d784f23953ed
出典データセット
uspto-grants-2013_03
特許番号
US08399491B2

反応ノート

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