Ammonium Chloride → HCID 58474459, compound

Participants

Reaction Conditions

Reaction Steps

To 7-chlorothienopyridine (0.81 g, 4.8 mmol) in THF (100 mL) at −78° C. was added n-butyllithium (2.5 M in hexanes, 2.1 mL, 5.1 mmol), dropwise. The mixture was allowed to warm to 0° C. then zinc chloride (1.0 M in diethyl ether, 4.8 mL, 4.8 mmol) was added. The mixture was stirred and warmed to room temperature. Bromide 175 (1.0 g, 3.7 mmol) and tetrakis(triphenylphosphine)palladium (0.85 g, 0.74 mmol) in THF (75 mL) were added dropwise, and the resultant mixture was heated to reflux for 2 h. It was then cooled and ammonium chloride (2.0 mL) was added, and the mixture was concentrated. The residue was partitioned between water and ethyl acetate, resulting in a thick precipitate. This was isolated by suction filtration and triturated with ethyl acetate, to provide title compound 176 (1.35 g, 100% yield, crude) as a yellow solid. LRMS (M+H): 360.4

Provenance & Evidence