Potassium Carbonate → 3-bromo-1-(4-chloromethylbenzyl)-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one (0.60 g, 2.5 mmol) in DMF (40 mL) was added K2CO3 (0.70 g, 5.1 mmol) and α,α′-dichloro-p-xylene (0.53 g, 3.0 mmol), and the reaction mixture was stirred at 110° C. for 2 h. The reaction mixture was cooled to room temperature, diluted with brine, and extracted with CHCl3 (4×100 mL). The combined organics were washed water and then brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to afford 3-bromo-1-(4-chloromethylbenzyl)-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one as an off-white solid (0.49 g, 43%): 1H NMR (300 MHz, CDCl3) δ 7.54 (app q, J=8 Hz, 1H), 7.38-7.28 (m, 5H), 6.94 (td, J=8, 2 Hz, 1H), 6.85 (td, J=8, 2 Hz, 1H), 6.10 (d, J=9 Hz, 1H), 5.21 (s, 2H), 5.16 (s, 2H), 4.56 (s, 2H).

Provenance & Evidence