Dimethyl Sulfoxide → HCID 68004132, compound

Participants

Reaction Conditions

Reaction Steps

To a sealed vessel were added 2-chloro-3-fluoro-5-bromopyridine (1) (10.50 g, 50 mmol), N-Boc-piperazine (9.30 g, 50 mmol), K2CO3 (8.28 g, 60 mmol), and DMSO (40 mL). The resulting mixture was heated at 120° C. for 12 hrs, then cooled down and diluted with ethyl ether (200 mL). The solution was washed with water (80 mL×2), brine (100 mL), dried, and concentrated. The residue was suspended in hexanes (150 mL) and the precipitation was formed. After removed the solid, the remaining solvents which contained the desired product were evaporated and subjected to chromatography column eluted with ethyl acetate/hexanes (0-10%) to afford 4.60 g (26%) of 11 as a colorless oil which was slowly solidified to be white solid. 1H NMR (CDCl3) δ 1.48 (9 H, s), 3.43 (4 H, m), 3.54 (4 H, m), 7.39 (4 H, dd, J=1.96, 12.04 Hz), 8.05 (1 H, m). LC/MS (M+1) 361.

Provenance & Evidence