Benzenesulfonyl chloride → 1-benzenesulfonyl-3-bromo-6-nitro-1H-indole

HRID 2284310

反応式

HRID 2284310 の反応式
[H-].[Na+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[N:6]([S:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:24])=[O:23])[CH:5]=1

参加物

5

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 147079343-Bromo-6-nitro-1H-indole

生成物 1

HCID 574421961-benzenesulfonyl-3-bromo-6-nitro-1H-indole収率 76.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (461 mg, 11.5 mmol) was slowly added to a solution of 3-bromo-6-nitro-1H-indole (2.32 g, 9.61 mmol) in tetrahydrofuran (10.0 mL). After stirring for 5 min, benzenesulfonyl chloride (1.47 mL, 11.5 mmol) was added dropwise over 10 min. The reaction was stirred an additional 1.5 h before quenching with 5.0 mL of methanol, followed by 10.0 mL water and 20.0 mL methylene chloride. The precipitate was filtered off and washed with an excess of methylene chloride and methanol to give a crème-colored powder for 3-bromo-6-nitro-1-(phenylsulfonyl)-1H-indole (2.80 g, 7.35 mmol, 76%).

後処理

  1. stirringThe reaction was stirred an additional 1.5 h
  2. custombefore quenching with 5.0 mL of methanol
  3. filtrationThe precipitate was filtered off
  4. washwashed with an excess of methylene chloride and methanol

出典と根拠

ORDレコード
ord-61e947e1665143c7be2c4f5506605dfa
出典データセット
uspto-grants-2015_09
特許番号
US09144557B2

関連ノート

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