7-Chlorothieno[3,2-b]pyridine → HCID 58790172, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-chlorothienopyridine (2.23 g, 13.1 mmol) in dry THF (50 mL) at −78° C. under N2 was added n-butyllithium (2.5 M in hexanes, 5.6 mL, 14 mmol), dropwise, with stirring. The resulting suspension was stirred for 30 min at −78° C., then ZnCl2 (0.5M in THF, 30 mL, 15 mmol) was added and the mixture was allowed to warm to 0° C. Imidazole 372 (3.20 g, 11.4 mmol) and tetrakis(triphenylphosphine)palladium (0.40 g, 0.35 mmol) in THF (50 mL) were then added to the aryllithium suspension, and the mixture was heated under reflux for 2 h, then cooled and concentrated. The residue was partitioned between ethyl acetate and water. The organic phase was collected, filtered, dried (anhydrous MgSO4), filtered again and concentrated. The resulting solid was triturated (1:1 ethyl acetate/hexanes) to afford 373 (1.62 g, 44% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.55 (d, J=5.1, 1H); 7.91 (d, J=1.2, 1H); 7.78 (d, J=1.2, 1H); 7.77 (s, 1H); 7.45 (d, J=5.2, 1H); 5.05 (s, 2H); 4.17 (q, J=7.2, 2H); 1.23 (t, J=7.0, 3H). LRMS (M+H): 322.0

Provenance & Evidence