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4-Toluenesulfonyl chloride → 5-bromo-1-(4-methylbenzenesulfonyl)-1H-indole-3-carbaldehyde

HRID 375984
Notes
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Reaction equation

HRID 375984 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]=[O:12].C([N-]C(C)C)(C)C.[Li+].O1CCCC1.[S:26](Cl)([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:26]([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH:6]=[C:5]2[CH:11]=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 701375-Bromoindole-3-carbaldehydeHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)

Product 1

HCID 103849695-bromo-1-(4-methylbenzenesulfonyl)-1H-indole-3-carbaldehydeYield 248.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent
2×

Procedure

To a solution of 5-bromoindole-3-carboxaldehyde (10 g) in dry tetrahydrofuran (75 ml), cooled to -78° C., was added with 2M lithium diisopropylamide/tetrahydrofuran (22.5 ml). After 30 min., the mixture was treated with a solution of tosyl chloride (9.5 g) in dry tetrahydrofuran (75 ml). The mixture was allowed to warm to room temperature overnight and evaporated. The residue was dissolved in dimethylformamide, filtered, and the filtrate was diluted with water. The precipitate was collected and recrystallized from ethanol to give 42 g (25%) of product.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in dimethylformamide
  3. filtrationfiltered
  4. additionthe filtrate was diluted with water
  5. customThe precipitate was collected
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3b2a10145c7b4cdfa7444fb262619b0d
Source dataset
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05488063

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes