Thieno(2,3-c)pyridine → HCID 22607601, compound

Participants

Reaction Conditions

Reaction Steps

A solution of thieno[2,3-c]pyridine (J. Wikel, et al., J. Heterocycl. Chem., 1993, 30, 289) (2.0 g, 14.8 mmol) in THF (50 mL) at −78° C. was treated with n-butyllithium (2.5 M solution in hexane, 7.1 mL, 17.8 mmol), warmed to 0° C., stirred for 15 minutes, cooled to −78° C., treated slowly with trimethyltin chloride (3.54 g, 17.8 mmol) in THF (10 mL), warmed to room temperature for 2 hours, and partitioned between ethyl acetate and brine. The ethyl acetate solution was washed with water, and concentrated. The residue was purified by flash chromatography (10-35% ethyl acetate in hexane) to provide the desired product (3.15 g, 71%). MS (APCI) m/e 298 (M+H)+.

Provenance & Evidence