Uses
2-Chloro-3-hydroxypyridine has been used in the preparation of 3-hydroxypyridine-2( 1 H)-selone. It has also been used in the synthesis of all four possible benzo[4,5]furopyridine tricyclic heterocycles: benzo[4,5]furo[2,3-b]pyridine, benzo[4,5]furo[2,3-c]pyridine, benzo[4,5]furo[3,2-c]pyridine, and benzo[4,5]furo[3,2-b]pyridine. the synthesis involves α and γ-activation of chloropyridines, as well as palladium-mediated reactions.
Synthesis
GENERAL METHOD: To a solution of 2-chloro-3-pyridyl trifluoromethanesulfonate (0.3 mmol) in anhydrous toluene (5 mL) was added Cs2CO3 (3 equiv). The reaction suspension was heated at 80 °C (oil bath temperature) with stirring for 15 hours. Upon completion of the reaction, the crude reaction mixture was quenched with ethyl acetate (~5 mL) and saturated aqueous ammonium chloride solution (~10 mL). The aqueous layer was separated and extracted with ethyl acetate (2 x 10 mL). The organic layers were combined, dried with anhydrous MgSO4 and concentrated under reduced pressure to give the crude product 2-chloro-3-hydroxypyridine. Finally, the product was purified by fast column chromatography on silica gel.
References
[1] Tetrahedron Letters, 2013, vol. 54, # 51, p. 7078 - 7079
