反应详情

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.

1. customquenched in sat. NaHCO3
2. extractionextracted with EtOAc (4×)
3. washThe combined organic layers were washed with brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by silica gel column chromatography in EtOAc with gradient to EtOAc:methanol (99:1)