Water → Tert-butyl (5-((trimethylsilyl)ethynyl)thiazol-2-yl)carbamate

HRID 1889179노트

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HRID 1889179 반응식
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[S:9][C:10](Br)=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17].O>C(N(CC)CC)C.[Cu]I>[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[S:9][C:10]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 21300388tert-butyl N-(5-bromo-1,3-thiazol-2-yl)carbamate

생성물 1

HCID 45117882Tert-butyl (5-((trimethylsilyl)ethynyl)thiazol-2-yl)carbamate수율 79.1%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8471Triethylamine용매

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온도
80 °C

실험 절차

(5-Bromo-thiazol-2-yl)-carbamic acid tert-butyl ester (2.0 g, 7.164 mmol) was taken in triethylamine (20 ml). To this solution was added CuI (0.041 g, 0.215 mmol), PdCl2 (PPh3)2 (0.050 g, 0.071 mmol) followed by the addition of trimethylsilylacetylene (1.055 g, 10.741 mmol). The reaction was heated at 80° C. overnight. Reaction mixture was cooled to room temperature and poured into water (50 ml), extracted with ethyl acetate (30 ml×3). The combined organic layer was washed with 1N HCl followed by brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The crude product was purified by column chromatography over silica gel using 6% ethyl acetate hexane as eluent to provide pure (5-trimethylsilanylethynyl-thiazol-2-yl)-carbamic acid tert-butyl ester (1.679 g).

후처리

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. extractionextracted with ethyl acetate (30 ml×3)
  4. washThe combined organic layer was washed with 1N HCl
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe crude product was purified by column chromatography over silica gel using 6% ethyl acetate hexane as eluent

출처 및 근거

ORD 기록
ord-1010db0214b7490c8ca6f9a895c9e6de
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501955B2

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