Reaktion #68815

Reaktionsgleichung

Triethylamine

2-Amino-5-iodopyridine

phenylacetylene

→

5-phenylethynyl-pyridin-2-ylamine

Ausbeute 62.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled
2. 2
   Extraktionextracted with saturated NaHCO3 solution and three times with ethyl acetate
3. 3
   Trocknendried over sodium sulfate
4. 4
   Sonstigeevaporated to dryness
5. 5
   Filtrationfiltered
6. 6
   Sonstigethe solid evaporated to dryness

Vorschrift

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+).

Quelle