Oxazolo[4,5-b]pyridine Chemical Properties

Melting point:

69-72 °C

Boiling point:

199.2±13.0 °C(Predicted)

Density 

1.294±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

-0.27±0.40(Predicted)

color 

Brown

Safety Information

HS Code 

2934999090

Oxazolo[4,5-b]pyridine Usage And Synthesis

Definition

ChEBI: Oxazolo[4,5-b]pyridine is a mancude organic heterobicyclic parent and an oxazolopyridine.

Synthesis

General procedure for the synthesis of oxazolo[4,5-b]pyridines from 2-amino-3-hydroxypyridine (90.1 mmol) and triethyl orthoformate (720.7 mmol): 2-amino-3-hydroxypyridine was dissolved in triethyl orthoformate under nitrogen protection, and p-toluenesulfonic acid (4.50 mmol) was added as catalyst. The reaction mixture was stirred at 160 °C overnight. Upon completion of the reaction, the excess of triethyl orthoformate was removed by distillation under reduced pressure. The crude product was purified by column chromatography with the eluent cyclohexane/ethyl acetate (5%-40% gradient elution) to afford oxazolo[4,5-b]pyridine as a beige solid in 68% yield. The product was detected by mass spectrometry (LRMS) with [M + H]+ m/z of 121.1; 1H NMR (DMSO-d6, 400 MHz) δ 9.04 (s, 1H), 8.58 (dd, J = 4.8, 1.4 Hz, 1H), 8.26 (dd, J = 8.2, 1.4 Hz, 1H), 7.50 (dd, J = 8.2, 4.8 Hz , 1H), 6.41 (s, 2H); 13C NMR (DMSO-d6, 101 MHz) δ 157.7, 154.5, 147.1, 142.0, 121.5, 120.1.

References

[1] Monatshefte fur Chemie, 2011, vol. 142, # 1, p. 87 - 91
[2] Journal of Organic Chemistry, 2011, vol. 76, # 13, p. 5444 - 5449
[3] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 450 - 465
[4] Tetrahedron Letters, 1990, vol. 31, # 8, p. 1155 - 1156
[5] Synthetic Communications, 1992, vol. 22, # 20, p. 2891 - 2901

Oxazolo[4,5-b]pyridine(273-97-2)Related Product Information

• 2-OXAZOLECARBONITRILE
• 2-OXAZOLEMETHANOL
• 5-ISOXAZOLEMETHANOL
• Oxazole-2-carbaldehyde
• ETHYL 2-OXAZOLECARBOXYLATE
• Oxazolo[4,5-c]pyridine-2(3H)-thione
• 5-OXAZOLECARBOXALDEHYDE
• Oxazolo[5,4-b]pyridin-2(1H)-one (6CI,9CI)
• OXAZOLO[4,5-B]PYRIDIN-2(3H)THIONE
• Oxazolo[4,5-c]pyridin-2(3H)-one
• 2,3-Dihydropyrido[2,3-d][1,3]oxazol-2-one
• Linezolid
• Mifepristone
• OXAZOLO[4,5-B]PYRIDIN-2-AMINE
• Oxazolo[4,5-c]pyridin-2-amine (9CI)
• Oxazolo[5,4-b]pyridine
• metamifop