Potassium Carbonate → 4-(5-Bromo-pyridin-2-ylmethyl)-thiomorpholine 1,1-dioxide

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-bromo-2-bromomethyl-pyridine (1.34 g, 5.34 mmol), thiomorpholine 1,1-dioxide (0.860 g, 6.36 mmol), and potassium carbonate (1.49 g, 10.8 mmol) in acetone (15.0 mL) was stirred at 40° C. overnight. The mixture was cooled to room temperature and the volatiles were evaporated. The residue was partitioned between EtOAc (100 mL) and saturated aqueous ammonium chloride (50 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-100% EtOAc/hex as the eluting solvent to obtain 4-(5-bromo-pyridin-2-ylmethyl)-thiomorpholine 1,1-dioxide as a white solid (1.37 g, 84%). m.p.=129-131° C.; LCMS (m/e) 305 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.64 (d, 1H, J=2.3 Hz), 8.82 (dd, 1H, J=2.3 and 8.3 Hz), 7.29 (d, 1H, J=8.3 Hz), 3.78 (s, 2H), 3.13-3.02 (m, 8H).

Provenance & Evidence