Cesium carbonate → HCID 67467679, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added 6-bromo-1,3-benzothiazol-2(3H)-one (11.1 g, 48.5 mmol), anhydrous NMP (10 mL), anhydrous 1,4-dioxane (100 mL), cesium carbonate (33.2 g, 102 mmol), followed by 2-(bromomethyl)-1,1-difluorocyclopropane (8.29 g, 48.5 mmol). The reaction mixture was then heated to 95° C. while stirring in a hot oil bath with a water cooled reflux condenser attached under an atmosphere of nitrogen for 18 hours. The crude reaction mixture was then cooled to room temperature, suspended in ethyl acetate and washed with a saturated solution of sodium bicarbonate, followed by water, then brine, dried over sodium sulfate, filtered, and concentrated. The resulting residue was then purified by silica gel chromatography (0-30% EtOAc/Hex) to give 6-bromo-3-[(2,2-difluorocyclopropyl)methyl]-1,3-benzothiazol-2(3H)-one (1-1) as a white solid. HRMS (M+H)+: observed=319.9550, calculated=319.9551.

Provenance & Evidence