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

HRID 1601184Notes

Reaction equation

HRID 1601184 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. 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-6a29e73279074b4ba8de9eeccdb423f9
Source dataset
uspto-grants-1999_11
Patent number
US05977147

Reaction notes

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