Potassium Carbonate → HCID 67065454, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-3-furancarboxamide (400 mg, 0.77 mmol) in dioxane/H2O (5:1, 50 mL) was added K2CO3 (0.32 g, 2.3 mmol), tetrakistriphenylphosphine Pd(0) (20 mg, 40 μmol) and 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (0.19 g, 0.92 mmol). The reaction mixture was heated to 75° C. in a sealed tube. After 5 h, additional tetrakistriphenylphosphine Pd(0) (20 mg, 40 μmol) and 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (0.19 g, 0.92 mmol) were added. After 8 h, the reaction solution was then partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organics were dried (Na2SO4), concentrated under vacuum and purified on silica gel (hexanes/EtOAc, 1:2) to give the title compound (200 mg, 50%) as white solid: LCMS (ES) m/z=523.

Provenance & Evidence