반응 #68815

반응 방정식

Triethylamine

2-Amino-5-iodopyridine

phenylacetylene

→

5-phenylethynyl-pyridin-2-ylamine

수율 62.0%

용매

THF

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled
2. 2
   추출extracted with saturated NaHCO3 solution and three times with ethyl acetate
3. 3
   건조dried over sodium sulfate
4. 4
   기타evaporated to dryness
5. 5
   여과filtered
6. 6
   기타the solid evaporated to dryness

실험 절차

Bis-(triphenylphosphine)-palladium(II)dichloride (480 mg, 0.68 mmol, 0.05 equiv.) was dissolved in 50 ml THF. (3 g, 13.6 mmol) 2-Amino-5-iodopyridine and phenylacetylene (2.79 g, 27.3 mmol, 2.0 equiv.) were added at room temperature. Triethylamine (5.58 ml, 40.9 mmol, 3 equiv.), triphenylphosphine (111 mg, 0.41 mmol, 0.03 equiv.) and copper(I)iodide (70 mg, 0.41 mmol, 0.03 equiv.) were added and the mixture was stirred for 2 hours at 65° C. The reaction mixture was cooled and extracted with saturated NaHCO3 solution and three times with ethyl acetate. The organic layers were combined, dried over sodium sulfate and evaporated to dryness. The crude product was suspended in dichloromethane, filtered and the solid evaporated to dryness. The desired 5-phenylethynyl-pyridin-2-ylamine (1.6 g, 62% yield) was obtained as a light yellow solid, MS: m/e=195.3 (M+H+).

출처