Pyridine → N-(3-(6-bromo-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

According to Scheme 2 Step 3: A mixture of 6-bromo-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-1,2,4-triazine-3,5(2H,4H)-dione (300 mg, 0.83 mmol), DMF (5 mL), 3-acetamidophenylboronic acid (222 mg, 1.24 mmol), copper acetate (150 mg, 0.83 mmol) and pyridine (135 μl, 1.66 mmol) was stirred at 65° C. for 15 hours under room atmosphere. A saturated solution of NaHCO3 (200 mL) was added and the aqueous layer was extracted thrice with 200 mL of DCM. The organic layers were combined to be dried over MgSO4, filtered and concentrated under reduced pressure to afford a brown solid. The crude solid was purified by flash chromatography with silica gel (AIT Flashmart 25 g prepacked column C18) using water/acetonitrile 6/4 as eluant to afford N-(3-(6-bromo-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide (250 mg, 61%) as a white solid.

Provenance & Evidence