Water → 5-Fluoro-1-(2-oxiranylmethyl)-1H-indole

HRID 1532616노트

반응식

HRID 1532616 반응식
[CH2:1]([CH:3]1[O:5][CH2:4]1)Br.[F:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2.[H-].[Na+].O>CN(C=O)C>[CH2:1]([N:12]1[C:13]2[C:9](=[CH:8][C:7]([F:6])=[CH:15][CH:14]=2)[CH:10]=[CH:11]1)[CH:3]1[O:5][CH2:4]1

참가 물질

6

반응물 4

HCID 962WaterHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 678615-Fluoroindole

생성물 1

HCID 155242005-Fluoro-1-(2-oxiranylmethyl)-1H-indole수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

Epibromohydrin (1.4 ml, 16.5 mmole) was added to a stirred solution of 5-fluoroindole (2.0 g, 15 mmole) and sodium hydride (0.66 g, 16.5 mmole) in anhydrous DMF (20 ml), and the mixture was heated at 60° C. under nitrogen for 15 hours. Water (100 ml) was added and the product extracted into CH2Cl2 (3×35 ml). The combined organics were washed with water (25 ml), brine (25 ml) and dried over anhydrous sodium sulfate. Filtration and concentration in vacuo gave the crude product as a viscous yellow colored oil (2.7 g). This was purified by flash silica gel chromatography (30% ethyl acetate in hexane) to afford the titled product as a viscous oil (2.5 g, 89% yield).

후처리

  1. extractionthe product extracted into CH2Cl2 (3×35 ml)
  2. washThe combined organics were washed with water (25 ml), brine (25 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationFiltration and concentration in vacuo
  5. customgave the crude product as a viscous yellow colored oil (2.7 g)
  6. customThis was purified by flash silica gel chromatography (30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-3b2fc20ab0e0475988855526f8b22525
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06204274B1

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