7-CHLORO-THIENO[2,3-C] PYRIDINE synthesis

Yield:-

Reaction Conditions:

in phosphorous oxy chloride;dichloromethane;

Steps:

61.C 4-Hydroxy-3-[3-(S)-(7-chloro-thieno[2,3-c]pyridine-2-sulfonylamino)-2-oxo-pyrrolidin-1-ylmethyl]-benzamidine trifluoroacetate.

C. 7-Chloro-thieno[2,3-c]pyridine. 6H-Thieno[2,3-c]pyridin-7-one (2.3 g, 15.22 mmol) is dissolved in 50 mL of phosphorous oxy chloride. The solution is heated to 100° C. After 4 hours, the solution is concentrated. The residue is dissolved in CH₂ Cl₂. The resulting solution is washed with water and saturated NaCl. The organic layer is dried over MgSO₄, filtered and concentrated. The crude product is purified by column chromatography eluding with a gradient of 40% CH₂ Cl₂ /hexanes to 60% CH₂ Cl₂ /hexanes. The title compound (2.0 g, 12.2 mmol) is obtained as a white solid. ¹ H NMR (CDCl₃, 300 MHz) δ8.26 (d, 1H), 7.76 (d, 1H), 7.62 (d, 1H), 7.41 (d, 1H). EI MS, [M]⁺ =169, 171, Cl pattern.

References:

US6034093,2000,A