HCID 11717093, compound → HCID 11559143, compound

Participants

Reaction Steps

Anhydrous THF (8 mL) was added to a mixture of potassium t-butoxide (140 mg, 1.27 mmol) and methyltriphenylphosphonium bromide (0.45 g, 1.27 mmol) under N2 atmosphere. The reaction was stirred for 30 min at room temperature. A solution of [2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-(6-methoxy-pyridin-2-yl)-methanone (0.29 g, 0.85 mmol) in THF (8 mL) was added and the reaction was stirred for 1 hour at room temperature. The reaction was quenched by the addition of 0.1N HCl until the pH was <3 and extracted with 0.1N HCl. The aqueous layers were made basic with NH4OH and extracted with EtOAc. The organic layers were washed with water and concentrated in vacuo. Mass triggered preparative HPLC afforded 190 mg of (2-{3-[1-(6-methoxy-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (Compound 15-1) as a TFA salt.

Provenance & Evidence