1-Pyrrolidineethanol → 2-(4-Methoxyphenyl)benzo[b]thiophen-3-yl 6-[2-(1-Pyrrolidinyl)ethoxy]pyrid-3-yl Ketone

Participants

Reaction Steps

A solution of 0.50 mL (4.30 mmol) of 1-(2-hydroxyethyl)pyrrolidine in 10 mL of xylenes was treated with 50 mg (2.20 mmol) of Na. The mixture was heated to 50° C. until all the Na had disappeared, cooled to room temperature, and then treated with a solution of 420 mg (1.10 mmol) of 2-(4-methoxyphenyl)benzo[b]thiophen-3-yl 6-chloropyrid-3-yl ketone (Part A) in 5 mL of xylenes. The reaction was heated to 50° C. for 2 h and was evaporated in vacuo. The residue was partitioned between H2O (50 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layers were dried over K2CO3 and evaporated in vacuo to give 810 mg of a yellow solid. Purification by radial chromatography (SiO2; gradient of 1-5% MeOH in CH2Cl2) gave 525 mg (1.09 mmol; 99%) of the title compound as an amber oil.

Provenance & Evidence