2,5-Dibromopyridine → 5-Bromo-2-(2-(pyrrolidin-1-yl)ethoxy)pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 8.00 g (69.6 mmol) of N-(2-hydroxyethyl)pyrrolidine in 150 mL of xylenes was treated with 534 mg (23.2 mmol) of Na and the mixture was heated to 80° C. until all the Na had disappeared. The reaction was cooled to 23° C. and 5.50 g (23.2 mmol) of 2,5-dibromopyridine was added. The mixture was stirred at room temperature for 2.25 h and was concentrated in vacuo. Purification by flash chromatography (SiO2; gradient of 50-70% EtOAc in hexanes) afforded 3.53 g (13.0 mmol; 56%) of the title compound.

Provenance & Evidence