Potassium Carbonate → HCID 67376212, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-4-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (0.230 mmol) in dioxane (1.5 mL) was treated with 5-bromo-1,3-benzothiazole (0.230 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane adduct (9 mg), and 2M aq potassium carbonate (0.690 mmol). The reaction mixture was purged with nitrogen, sealed, and stirred at 100° C. overnight. The reaction mixture was cooled to room temperature and was diluted with water (50 mL). The aqueous layer was acidified to pH˜4 using 1N aq HCl and was extracted with dichloromethane. The organic layer was dried over magnesium sulfate, treated with Si-Thiol (Silicycle, 20 mg), filtered, and concentrated in vacuo. Silica gel chromatography (0-8% methanol/dichloromethane) and reverse phase HPLC (20-50% acetonitrile w/0.1% TFA/water w/0.1% TFA) were utilized in purifying this compound. The product fractions from the HPLC were combined, adjusted to pH˜5 with the addition of saturated aq sodium bicarbonate, and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo, providing the title compound as an amorphous off-white solid (39%). MS(ES)+ m/e 464.3 [M+H]+.

Provenance & Evidence