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

HRID 1532616ノート

反応式

HRID 1532616 の反応式
[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

参加物

6

反応物 4

HCID 962WaterHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 678615-Fluoroindole

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3b2fc20ab0e0475988855526f8b22525
出典データセット
uspto-grants-2001_03
特許番号
US06204274B1

反応ノート

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