Lithium borohydride → 5-bromo-7-ethyl-1H-indole

HRID 2249529ノート

反応式

HRID 2249529 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][CH3:12])[CH:10]=1)[NH:7][C:6](=O)[C:5]2=O.[BH4-].[Li+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][CH3:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

参加物

4

反応物 2

HCID 4148881Lithium borohydrideHCID 80338135-Bromo-7-ethylindoline-2,3-dione

生成物 1

HCID 210715755-bromo-7-ethyl-1H-indole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
90 °C

実験手順

To a solution of 5-bromo-7-ethyl-1H-indole-2,3-dione (36.0 g, 144 mmol) in tetrahydrofuran (120 mL) at room temperature was dropped a 2.0 M solution of lithium borohydride in tetrahydrofuran. The reaction mixture was stirred at 90° C. (oil bath) for 5 hours. After cooling down to room temperature, it was quenched with 5% hydrochloric acid solution until the excess lithium borohydride was destroyed. To the mixture was added saturated sodium bicarbonate solution (300 mL) and extracted with ethyl acetate. Extracts were dried over magnesium sulfate and concentrated under reduced pressure to give the crude product of 5-bromo-7-ethyl-1H-indole, which went to next reaction without further purification.

後処理

  1. temperatureAfter cooling down to room temperature
  2. customit was quenched with 5% hydrochloric acid solution until the excess lithium borohydride
  3. customwas destroyed
  4. additionTo the mixture was added saturated sodium bicarbonate solution (300 mL)
  5. extractionextracted with ethyl acetate
  6. dry with materialExtracts were dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6addc04c770341d6b629519ca5476b86
出典データセット
uspto-grants-2008_01
特許番号
US07314886B2

反応ノート

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