[N+:1]([C:4]1[CH:9]=[CH:8][C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][C:5]=1[NH:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21])([O-:3])=[O:2].C(=O)(O)[O-].[Na+].Br[C:33]1[CH:38]=[N:37][CH:36]=[CH:35][N:34]=1>[Pd]>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:33]2[CH:38]=[N:37][CH:36]=[CH:35][N:34]=2)=[CH:6][C:5]=1[NH:19][C:20]([N:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1)=[O:21])([O-:3])=[O:2]To a solution of N-(2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidine-1-carboxamide (0.20 g, 0.55 mmol) was added at room temperature sodium bicarbonate (0.09 g, 0.80 mmol, 1.45 equiv.), 2-bromopyrazine (0.14 g, 0.89 mmol, 1.6 equiv.) and palladium (0.07 g, 0.06 mmol, 0.1 equiv). The reaction was refluexed for fourteen hours. The crude reaction was filtered and concentrated. The residue was diluted into water and washed with ethyl acetate, the concentrated. The obtained was purified through column chromatography by eluting ethyl acetate and hexane to allow N-(2-nitro-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide (0.12 g, 70% yield).
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