Potassium Phosphate, Tribasic → HCID 67409967, compound

Participants

Reaction Conditions

Reaction Steps

1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (12-1) (2.0 g, 5.0 mmol, 1 eq), 2-chloro-4-hydroxybenzonitrile (0.84 g, 5.5 mmol, 1.1 eq), tripotassium phosphate (2.1 g, 10.0 mmol, 2.0 eq), S-Phos (0.20 g, 0.5 mmol, 0.1 eq), and palladium(II) acetate (56 mg, 0.25 mmol, 0.05 eq) were combined in dioxane (20 mL) and water (3 mL). The resulting mixture was heated at 100° C. for 16 hours. The reaction mixture was allowed to cool to room temperature. The mixture was then diluted with EtOAc (100 mL), washed with water (20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography (80 g SiO2, 0-80% EtOAc in hexanes) to afford 2-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl}-4-hydroxybenzonitrile (12-2) as a white solid. LRMS m/z (M+H) 392.3 found, 392.1 required.

Provenance & Evidence