p-Bromobenzenesulfonyl chloride → ethyl 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carboxylate

HRID 2264625Notes

Reaction equation

HRID 2264625 reaction equation
CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]1[C:34]([O:36][CH2:37][CH3:38])=[O:35].[Br:39][C:40]1[CH:45]=[CH:44][C:43]([S:46](Cl)(=[O:48])=[O:47])=[CH:42][CH:41]=1>C1COCC1.C(OCC)(=O)C>[Br:39][C:40]1[CH:45]=[CH:44][C:43]([S:46]([N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[C:26]2[C:34]([O:36][CH2:37][CH3:38])=[O:35])(=[O:48])=[O:47])=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 2855718-Crown-6HCID 73125Ethyl indole-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67043967ethyl 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carboxylateYield 95.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.5 g of potassium t-butoxide and 0.1 g of 18-crown-6 in 3 mL of THF, a mixed solution of 0.7 g of ethyl 1H-indole-2-carboxylate and 3 mL of THF was added, and the resulting mixture was stirred at room temperature for 30 minutes. The solution was cooled with ice, 1.13 g of 4-bromobenzenesulfonyl chloride was added, and the resulting mixture was stirred at room temperature for 5 hours. To the solution was added 60 mL of ethyl acetate, the resulting mixture was washed with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:5) to obtain 1.44 g of ethyl 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carboxylate as a pale yellow syrup. FAB+: 408, 410

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature for 5 hours
  3. washthe resulting mixture was washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:5)

Sources & evidence

ORD record
ord-d6d5cf222d6e411eb1e67403140e4b05
Source dataset
uspto-grants-2010_12
Patent number
US07855225B2

Reaction notes

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