Potassium triisopropylsilanethiolate → 5-Triisopropylsilanylsulfanyl-indole-1-carboxylic acid tert-butyl ester

HRID 883950

Reaction equation

HRID 883950 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](I)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:18]([Si:21]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[S-:22])([CH3:20])[CH3:19].[K+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([S:22][Si:21]([CH:23]([CH3:25])[CH3:24])([CH:26]([CH3:28])[CH3:27])[CH:18]([CH3:19])[CH3:20])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11085560Potassium triisopropylsilanethiolateHCID 161259585-Iodo-1H-indole, N-BOC protected

Product 1

HCID 670403485-Triisopropylsilanylsulfanyl-indole-1-carboxylic acid tert-butyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 59A (200 mg, 0.583 mmol) in anhydrous tetrahydrofuran (4 mL) under a nitrogen atmosphere was treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium methylene chloride complex (5 mg) and the solution was sparged with nitrogen for several minutes. Potassium triisopropylsilanethiolate (146.5 mg, 0.6411 mmol), prepared according to Tetrahedron Letters 35 (20) 3221 1994, was added and the reaction was heated at reflux for 15 minutes. The reaction was cooled to room temperature and the solvent removed by rotary evaporation under vacuum to provide the title compound as a colorless oil (210 mg, 89%).

Workup

  1. customthe solution was sparged with nitrogen for several minutes
  2. additionwas added
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 15 minutes
  5. customthe solvent removed by rotary evaporation under vacuum

Sources & evidence

ORD record
ord-46c7a3ed112d49d8b750db64fa1c2a44
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Linked notes

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