[CH2:1]([N:4]1[C:9](=[O:10])[C:8]([Br:11])=[N:7][NH:6][C:5]1=[O:12])[CH:2]=[CH2:3].[C:13]([NH:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)(=[O:15])[CH3:14].N1C=CC=CC=1>CN(C=O)C.C([O-])(O)=O.[Na+].C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([N:4]1[C:9](=[O:10])[C:8]([Br:11])=[N:7][N:6]([C:21]2[CH:22]=[C:17]([NH:16][C:13](=[O:15])[CH3:14])[CH:18]=[CH:19][CH:20]=2)[C:5]1=[O:12])[CH:2]=[CH2:3]
According to Scheme 3 Step 2: A mixture of compound 6(A) (1.10 g, 4.74 mmol), 3-acetamidophenylboronic acid (1.20 g, 6.64 mmol), copper acetate (258 mg, 1.42 mmol) and pyridine (229 μL, 2.84 mmol) in DMF (30 mL) was stirred at 65° C. during 15 h under room atmosphere. The mixture was diluted with 50 mL of a saturated solution of NaHCO3 and the aqueous layer was extracted twice with 60 mL of DCM. The organic layers were combined dried over MgSO4, filtered filtrated and concentrated under reduce pressure to afford a brown solid. The crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 10 g SiO2) (Eluant: CH2Cl2/MeOH 98/2) to afford N-(3-(4-allyl-6-bromo-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 6(B) (800 mg, 46%) as a colorless oil.
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