Sodium borohydride → {2-[3-(2-Fluoro-pyridin-3-ylmethyl)-benzo[b]thiophen-2-yl]-ethyl}-dimethyl-amine

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Reaction Steps

A suspension of NaBH4 (0.11 g, 2.9 mmol) in 7 mL TFA was stirred at room temperature for 15 minutes. A solution of [2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-(2-fluoro-pyridin-3-yl)-methanol (0.12 g, 0.36 mmol) in 6 mL TFA was added slowly. The mixture was stirred at room temperature for 48 h. The solvent was evaporated and water and ammonium hydroxide were added at 0° C. until pH=9. The solution was extracted with EtOAc (3×) and washed with water/ammonium hydroxide (30/1 v/v). The combined organic layers were concentrated and 0.12 g of crude material was obtained. Purification by Mass triggered HPLC afforded 32 mg of {2-[3-(2-fluoro-pyridin-3-ylmethyl)-benzo[b]thiophen-2-yl]-ethyl}-dimethyl-amine (Compound 24-2) (MH+=315.0, tR=4.50, Method 2).

Provenance & Evidence