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

HRID 865442Notes

Reaction equation

HRID 865442 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]

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 8028TetrahydrofuranSolvent2×

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. Tile residue was dissolved in dimethylforrnamide, 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. dissolutionTile residue was dissolved in dimethylforrnamide
  3. filtrationfiltered
  4. additionthe filtrate was diluted with water
  5. customThe precipitate was collected
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-88031f59d89f4f68ac3ad9ba397f36e9
Source dataset
uspto-grants-1996_10
Patent number
US05565584

Reaction notes

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