Cesium carbonate → HCID 21182868, compound

Participants

Reaction Steps

A solution of 7-fluoro-2-[4-hydroxyphenyl]-6-methoxybenzo[b]thiophene (Part C; 550 mg, 2.0 mmol), 1-(2-chloroethyl)pyrrolidine hydrochloride (375 mg, 2.2 mmol) and Cs2CO3 (1.65 g, 5.0 mmol) in 20 mL of DMF was heated at 80° C. for 5 h. The reaction mixture was cooled to ambient temperature and poured into saturated aqueous NaHCO3 solution (20 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The combined organics were washed with H2O (2×50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by radial chromatography (SiO2; 2% MeOH in CHCl3, saturated with NH4OH) afforded 598 mg (1.61 mmol; 80%) of the title compound as a yellow oil.

Provenance & Evidence