4-Fluorobenzoyl chloride → [2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-(4-fluoro-phenyl)-methanone

Participants

Reaction Steps

To a solution of (2-Benzo[b]thiophen-2-yl-ethyl)-dimethylamine (Compound 1a, 1.1 mmol) in dichloroethane (1 mL) under N2 at 0° C., p-fluorobenzoyl chloride (1.32 mmol) and aluminum chloride (3.3 mmol, 1M in nitrobenzene) were added. The mixture was warmed to RT and stirred for 5 hrs, quenched in sat. NaHCO3 and extracted with EtOAc (4×). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography in EtOAc with gradient to EtOAc:methanol (99:1) as required. Compound 3-1, [2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-(4-fluoro-phenyl)-methanone, was isolated in 47% yield (170 mg); MS (MH+)=327.8.

Provenance & Evidence