4-Toluenesulfonyl chloride → HCID 18355197, compound

HRID 429614Notes

Reaction equation

HRID 429614 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C:6]=2[CH:5]=[CH:4]1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>O1CCCC1>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([N:3]2[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([C:12]([O:14][CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[O:13])[C:6]=3[CH:5]=[CH:4]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 12825939Benzyl 1H-indole-4-carboxylate

Product 1

HCID 18355197HCID 18355197, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (133 mg) in tetrahydrofuran (5.0 ml) was added dropwise a solution of benzyl indole-4-carboxylate (580 mg) in tetrahydrofuran (5.0 ml) at 0° C. and the mixture was stirred at 0° C. for 1 hour. 4-Toluenesulfonyl chloride (440 mg) was added to the mixture and the solution was stirred at ambient temperature for 1 hour. The reaction was quenched with 1N hydrochloric acid and then the aqueous solution was extracted with ethyl acetate. Drying, filtering and removal of solvents afforded a crude product. The crude product was purified by column chromatography (eluent; n-hexane:ethyl acetate=15:1) to give benzyl 1-(4-toluenesulfonyl)indole-4-carboxylate (560 mg) as a colorless syrup.

Workup

  1. stirringthe solution was stirred at ambient temperature for 1 hour
  2. customThe reaction was quenched with 1N hydrochloric acid
  3. extractionthe aqueous solution was extracted with ethyl acetate
  4. customDrying
  5. filtrationfiltering
  6. customremoval of solvents
  7. customafforded a crude product
  8. customThe crude product was purified by column chromatography (eluent; n-hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-9479b6873ffe4858a9af928dae6340fa
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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