Sodium Iodide → 4-[3-Chloro-2-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-benzo[b]thiophen-6-yloxymethyl]-benzoic acid methyl ester

Participants

Reaction Steps

Charge a vial with 3-(3-chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one (175 mg, 0.481 mmol) and dissolve in acetone (0.3 M). Add NaI (72 mg, 0.481 mmol) and Cs2CO3 (1.25 g, 3.85 mmol) and stir at room temperature for 5 minutes. Add 4-bromomethyl-benzoic acid methyl ester (220 mg, 0.96 mmol) and heat to 50° C. overnight. Cool to room temperature, filter, concentrate, and purify over silica gel to afford 4-[3-chloro-2-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-benzo[b]thiophen-6-yloxymethyl]-benzoic acid methyl ester. Dissolve in ethanol (5 mL) and water (1 mL) and add potassium hydroxide (162 mg, 2.88 mmol) and heat to 50° C. overnight. Cool to room temperature filter and dry to afford the title compound (146 mg, 61%) as a white solid: Mass spectrum (apci) m/z=498.2 (M+H).

Provenance & Evidence