Aluminium lithium hydride → 5-bromo-2-pyrrolidin-1-ylmethyl-1H-indole

HRID 591684

반응식

HRID 591684 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=O)=[CH:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[CH:5]2

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 471546575-Bromo-2-(pyrrolidine-1-carbonyl)-1H-indole

생성물 1

HCID 666709455-bromo-2-pyrrolidin-1-ylmethyl-1H-indole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a suspension of (5-bromo-1H-indol-2-yl)-pyrrolidin-1-yl-methanone (0.53 g, 1.8 mmol) in THF (50 mL) at 0° C. was slowly added lithium aluminum hydride (0.20 g, 5.4 mmol). The mixture was stirred under nitrogen at 0° C. for a while and the cooling bath was allowed to warm to room temperature. The mixture was then stirred at room temperature for 17 hours. The reaction was quenched by careful, successive, dropwise addition of water (0.2 mL), 15% NaOH aqueous solution (0.2 mL), and water (0.6 mL). The solid was filtered and washed with MeOH and CH2Cl2. The filtrate was concentrated to dryness, and dried under vacuum, to give 5-bromo-2-pyrrolidin-1-ylmethyl-1H-indole as a white solid. Yield: 0.45 g (90%).

후처리

  1. temperatureto warm to room temperature
  2. stirringThe mixture was then stirred at room temperature for 17 hours
  3. customThe reaction was quenched by careful, successive,
  4. additiondropwise addition of water (0.2 mL), 15% NaOH aqueous solution (0.2 mL), and water (0.6 mL)
  5. filtrationThe solid was filtered
  6. washwashed with MeOH and CH2Cl2
  7. concentrationThe filtrate was concentrated to dryness
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-86cf673281594b42bc32b56e1de6efda
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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