furo[3,2-b]pyridine Chemical Properties

Boiling point:

79-80℃ (12 Torr)

Density 

1.2g/ml

refractive index 

1.5753 (19℃)

storage temp. 

Inert atmosphere,Room Temperature

form 

liquid

pka

4.22±0.30(Predicted)

color 

Clear Colourless

Safety Information

HS Code 

2933399990

furo[3,2-b]pyridine Usage And Synthesis

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 23, p. 665, 1986 DOI: 10.1002/jhet.5570230305

Synthesis

PdCl2(PPh3)2 (1.4 g, 2.0 mmol) and CuI (0.4 g, 2.1 mmol) were dissolved in a solvent mixture of triethylamine (TEA, 100 mL) and tetrahydrofuran (THF, 200 mL) under nitrogen atmosphere. Subsequently, a solution of 2-bromo-3-acetoxypyridine (13.1 g, 60.6 mmol) and trimethylsilylacetylene (TMS-acetylene, 7.0 g, 71 mmol) in THF (100 mL) was added one time to the above solution. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution (50 mL) and methanol (50 mL). The mixture was continued to be stirred at 80 °C for 2 hours. After cooling to room temperature, it was extracted with ether. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The residue was purified by column chromatography to afford furo[3,2-b]pyridine (1.54 g, 21% yield).1H NMR (CDCl3, 400 MHz) δ 8.55 (m, 1H), 7.84 (m, 1H), 7.75 (m, 1H), 7.72 (m, 1H), 6.99 (m, 1H).

References

[1] Patent: WO2005/51304, 2005, A2. Location in patent: Page/Page column 144
[2] Patent: WO2005/51304, 2005, A2. Location in patent: Page/Page column 144

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