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

HRID 2284310

반응식

HRID 2284310 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-61e947e1665143c7be2c4f5506605dfa
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09144557B2

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