Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].[CH3:13][NH:14][C:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)=[O:16].C(=O)([O-])[O-].[Na+].[Na+]>O(C(OC)C)C.O>[Cl:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([CH3:12])=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([C:15]([NH:14][CH3:13])=[O:16])=[CH:18][CH:19]=2)[CH:7]=1To a mixture of the crude product from Step 1 (400 mg, 1.6 mmol), 4-(methylcarbamoyl)phenylboronic acid (286 mg, 1.6 mmol) and sodium carbonate (340 mg, 3.2 mmol) in dimethoxylethane/water (12/4 mL), is added palladium tetrakis(triphenylphospine) (93 mg, 5% mmol). The mixture is purged with N2 for 3 min, then sealed and heated at 90° C. for 3 h. The mixture is cooled, filtered and concentrated. The residue is purified with silica gel chromatography (30% ethyl acetate in DCM) to afford 5′-chloro-N,2′-dimethyl-4′-nitrobiphenyl-4-carboxamide as yellow solid. ESMS m/z 305.1 (M+H+).
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