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

HRID 883950

반응식

HRID 883950 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-46c7a3ed112d49d8b750db64fa1c2a44
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236950B2

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