Potassium Iodide → HCID 67468126, compound

Participants

Reaction Steps

To a round bottom flask was added 6-amino-7-bromo-3-[(2,2-difluorocyclopropyl)methyl]-1,3-benzothiazol-2(3H)-one (13-3) (0.205 g, 0.612 mmol), Dioxane (2.5 mL), water (2.0 mL), potassium iodide (1.015 g, 6.12 mmol), and 4-methylbenzenesulfonic acid hydrate (0.349 g, 1.835 mmol), then dropwise addition of a solution of sodium nitrite (0.084 g, 1.223 mmol) in water (0.5 mL). Reaction mixture was then stirred at room temperature for a few hours, then heated to 75 C in a hot oil bath with stirring overnight (˜15 hours). The reaction mixture was then cooled to room temperature then suspended in EtOAc, washed with sat'd Na2S2O3, then with sat'd NaHCO3, then water, then brine. Organics were then dried over Na2SO4 filtered & concentrated. Purification of crude reaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 40% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water) gave 7-bromo-3-[(2,2-difluorocyclopropyl)methyl]-6-iodo-1,3-benzothiazol-2(3H)-one (13-4) as a pink solid. HRMS (M+H)+: observed=445.852, calculated=445.8517.

Provenance & Evidence