4-Toluenesulfonyl chloride → 5-Fluoro-3-(3-p-toluenesulfonyloxypropyl)indole

HRID 1596781ノート

反応式

HRID 1596781 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][OH:14].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][O:14][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 150205413-(5-fluoro-1H-indol-3-yl)propan-1-ol

生成物 1

HCID 150205425-Fluoro-3-(3-p-toluenesulfonyloxypropyl)indole収率 79%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a stirred solution of 3-(5-fluoro-1H-indol-3-yl)-propan-l-ol (2.90 g, 15.0 mmol) in pyridine (15.0 mL) was added p-toluenesulfonyl chloride (7.1 g, 37.5 mmol) at room temperature. After stirring for 30 minutes at room temperature, the reaction mixture was poured to 200 nm of ice water. The aqueous was extracted with ethyl acetate and the combined organic extracts were washed with IN HCI and brine. The resulting material was dried over anhydrous sodium sulfate, filtered, and the solvent was concentrated under vacuum. The crude product was purified by silica gel column chromatography (ethyl acetatehexane, 3n) to give 4.1 g (79%) of the title compound as a solid: mp 74 CC (Lit. mp 99 ° C.; EP 464604 A2).

後処理

  1. extractionThe aqueous was extracted with ethyl acetate
  2. washthe combined organic extracts were washed with IN HCI and brine
  3. dry with materialThe resulting material was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe solvent was concentrated under vacuum
  6. customThe crude product was purified by silica gel column chromatography (ethyl acetatehexane, 3n)

出典と根拠

ORDレコード
ord-ac37f212a5d84d8ebf7481c256366770
出典データセット
uspto-grants-2001_09
特許番号
US06291683B1

反応ノート

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