Sodium Bicarbonate → 3-(Benzyloxy)-5-bromo-1-(difluoromethyl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

3-(Benzyloxy)-5-bromo-2-chloropyridine (100 mg, 0.335 mmol), 2-(fluorosulfonyl)difluoroacetic acid (179 mg, 1.005 mmol), and NaHCO3 (30 mg, 0.357 mmol) were combined in CH3CN (2 mL) then heated to 50° C. After heating overnight the mixture was cooled to RT and diluted with EtOAc. The resulting mixture was filtered through a pad of Celite® and concentrated. Flash column (Biotage-SNAP-10 g, 0-10% EtOAc/hexanes) gave the title compound (38 mg, 34%) as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.69 (t, J=60.06 Hz, 1 H); 7.42-7.35 (m, 5 H); 7.22 (d, J=2.2 Hz, 1 H); 6.68 (d, J=2.3 Hz, 1 H); 5.10 (s, 2 H).

Provenance & Evidence