Methanesulfonic Acid → (2-{3-[1-(5-Fluoro-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine

Participants

Reaction Steps

To a solution of 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-1-(5-fluoro-pyridin-2-yl)-ethanol in (1.65 g, 4.79 mmol) in methylene chloride (30 mL) at room temperature, methanesulfonic acid (310 uL, 4.8 mol) was added dropwise and the reaction was allowed to stir for 2 hours. Additional methanesulfonic acid (3.1 mL, 47.9 mmol) was added and the reaction was stirred for 2 more hours. The reaction was neutralized with aq NH4OH and was extracted with methylene chloride. Organic layer was concentrated. The reaction mixture was chromatographed on silica gel with 9:1 DCM:MeOH as eluent to afford 923 mg of (2-{3-[1-(5-fluoro-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (Compound 7-2) (59%).

Provenance & Evidence