Pyridine → HCID 68704513, compound

Participants

Reaction Steps

According to Scheme 2 Step 3: To a solution of 6-bromo-4-(4-chlorobenzyl)-1,2,4-triazine-3,5(2H,4H)-dione (0.600 g, 1.9 mmol) in DCM (8 ml) were added 3-cyanophenylboronic acid (0.42 g, 2.8 mmol), copper(II) acetate (0.069 g, 0.38 mmol), pyridine (0.3 g, 3.8 mmol) and pyridine N-oxide (0.2 g, 2.1 mmol) and the mixture was stirred overnight at room temperature. The reaction mixture was quenched with a saturated sodium bicarbonate solution and extracted with ethyl acetate (×3). The combined organic layers were washed with water then with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography, 30 g prepacked column, cycloexane/ethyl acetate 85/15 to afford 3-(4-(4-chlorobenzyl)-6-bromo-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)benzonitrile (300 mg, 38%) which was used in the next step without any purification

Provenance & Evidence