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

HRID 2069539ノート

反応式

HRID 2069539 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

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.

後処理

  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

出典と根拠

ORDレコード
ord-bca8f73f7e614fbca7a6df27c15e8366
出典データセット
uspto-grants-2012_10
特許番号
US08299114B2

反応ノート

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