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

HRID 2284310Notes

Reaction equation

HRID 2284310 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-61e947e1665143c7be2c4f5506605dfa
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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