反应 #1702160

反应方程式

(Trimethylsilyl)acetylene

tert-butyl (5-bromopyridin-3-yl)carbamate

triethylamine

→

desired product

收率 63.0%

tert-Butyl {5-[(trimethylsilyl)ethynyl]pyridin-3-yl}carbamate

收率 63.0%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   workup.ADDITIONwere then added
2. 2
   其他The solvent was removed under vacuum
3. 3
   workup.ADDITIONthe residue was diluted with EtOAc and water
4. 4
   其他After separation
5. 5
   干燥the organic layer was dried over Na2SO4
6. 6
   浓缩concentrated under vacuum
7. 7
   其他The crude product was purified by silica gel column chromatography

实验过程

Into a reaction flask were added tert-butyl (5-bromopyridin-3-yl)carbamate (3.0 g, 11.0 mmol), tetrahydrofuran (30 mL), and triethylamine (1.7 mL, 12 mmol). The reaction mixture was stirred under N2 bubbling for 5 min. (Trimethylsilyl)acetylene (1.60 g, 16.3 mmol), copper(I) iodide (84 mg, 0.44 mmol), and bis(triphenylphosphine)palladium(II) chloride (0.31 g, 0.44 mmol) were then added. The resultant mixture was heated at 50° C. overnight. The solvent was removed under vacuum and the residue was diluted with EtOAc and water. After separation, the organic layer was dried over Na2SO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired product as a white powder (2.0 g, 63%). LCMS for C15H23N2O2Si (M+H)+: m/z=291.1.

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