Sodium Hydroxide → 6-fluoro-2,3-dihydro-1H-indole

HRID 557223

반응식

HRID 557223 반응식
C([BH3-])#N.[Na+].[F:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1.[OH-].[Na+]>C(O)(=O)C>[F:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][NH:12]2)=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 3512786-FluoroindoleHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 2604006-fluoro-2,3-dihydro-1H-indole수율 76%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Add sodium cyanoborohydride (5.57 g, 88.78 mmol) to a solution of 6-fluoro-indole (10 g, 73.99 mmol) in acetic acid (100 ml). Stir at room temperature for 30 minutes. Pour the reaction mixture into 5N sodium hydroxide and extract with ethyl acetate. Wash the combined organic phases with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride. Concentrated under reduced pressure and subject the residue to silica gel chromatography to provide the desired compound as a colorless oil (7.69 g, 76%).

후처리

  1. extractionextract with ethyl acetate
  2. washWash the combined organic phases with saturated aqueous sodium bicarbonate
  3. concentrationConcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5876ebfc213c4646997de813d5d3e5d2
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058425B2

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