| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
|
| Company Name: |
Energy Chemical
|
| Tel: |
021-021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
|