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

HRID 1889179ノート

反応式

HRID 1889179 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8471Triethylamine溶媒

反応条件

温度
80 °C

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-1010db0214b7490c8ca6f9a895c9e6de
出典データセット
uspto-grants-2013_08
特許番号
US08501955B2

反応ノート

読み込み中…