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

HRID 605131

Reaction equation

HRID 605131 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 89A (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-65c3cecac44545a8b811602e59d70c79
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Linked notes

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