반응 #162368

반응 방정식

2-fluoro-3-iodopyridine

trimethylsilylacetylene

triethylamine

→

desired product

수율 85.9%

2-fluoro-3-[(trimethylsilyl)ethynyl]pyridine

수율 85.9%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   추출The reaction was extracted with EtOAc
2. 2
   세척washed with brine
3. 3
   건조dried over MgSO4
4. 4
   농축concentrated under vacuum
5. 5
   기타The product was purified by column chromatography on silica gel (10% ethyl acetate 90% hexanes)

실험 절차

Into a 1-neck round-bottom flask was added 2-fluoro-3-iodopyridine (1.0 g, 0.0045 mol), trimethylsilylacetylene (0.95 mL, 6.7 mmol), bis(triphenylphosphine)palladium(II) chloride (0.2 g, 0.2 mmol), copper(I) iodide (0.07 g, 0.4 mmol), and triethylamine (0.94 mL, 6.7 mmol) in N,N-dimethylformamide (20 mL). The reaction was stirred at 25° C. for 16 hours. The reaction was extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated under vacuum. The product was purified by column chromatography on silica gel (10% ethyl acetate 90% hexanes) to give 0.747 g of the desired product. 1H NMR (400 MHz, CDCl3): δ 7.86-7.89 (m, 1H), 7.55-7.61 (m, 1H), 6.86-6.90 (m, 1H). MS [M+H]=194.0

출처