Pyridine → 6-(4-Bromo-phenyl)-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one

Participants

Reaction Steps

Add pyridine (0.62 mL, 7.64 mmol) and triethylamine (0.53 mL, 3.82 mmol) to a mixture of 2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one (0.5 g, 1.91 mmol), 4-bromobenzeneboronic acid (1.15 g, 5.73 mmol), cupric acetate (1.05 g, 5.73 mmol), and 4A molecular sieves (0.4 g) in dichloromethane (38 mL). Stir the mixture at RT for 2 days. Dilute the mixture with CH2Cl2, wash twice with a solution of 5% NH4OH/H2O, and H2O. Dry the organics over Na2SO4, filter, wash with Et2O, and concentrate. Purify the crude material by flash chromatography eluting with 10-15% EtOAc/CH2Cl2 to give 0.2 g (25%) of the title compound. LC-ES/MS m/z (81Br, 35Cl) 417.8 [M+H]+.

Provenance & Evidence