Cl[C:2]1[C:3]([CH2:8][NH:9][C:10]([CH:12]2[CH2:16][C:15](=[O:17])[N:14]([CH3:18])[CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1.[C:19](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[CH3:18][N:14]1[C:15](=[O:17])[CH2:16][CH:12]([C:10]([NH:9][CH2:8][C:3]2[C:2]([CH3:19])=[N:7][CH:6]=[CH:5][N:4]=2)=[O:11])[CH2:13]1To a stirred suspension of N-((3-chloropyrazin-2-yl)methyl)-1-methyl-5-oxopyrrolidine-3-carboxamide (700 mg, 2.61 mmol) and potassium carbonate (540 mg, 3.91 mmol) in 1,4-dioxan (10 ml) under a nitrogen atmosphere was added trimethylboroxine (981 mg, 7.82 mmol) and 1,1′-bis-(diphenylphosphino)-ferrocene) palladium dichloride (214 mg, 0.261 mmol). The reaction was heated at 100° C. for one hour. Then the reaction mixture was filtered over celite and the celite was rinsed three times with ethyl acetate. Subsequently, the combined filtrates were concentrated in vacuo and the crude product was purified by column chromatography (silica gel; dichloromethane/methanol 96/5) to give 1-methyl-N-((3-methylpyrazin-2-yl)methyl)-5-oxopyrrolidine-3-carboxamide (440 mg).
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