Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[BH:17]([O-:19])[O-:18].C([O-])(=O)C.[K+].[CH3:25][CH:26]([C:28]1[CH:33]=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)[CH:29]=1)[CH3:27]>O1CCOCC1>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:17]3[O:19][C:28]([CH3:33])([CH3:29])[C:26]([CH3:27])([CH3:25])[O:18]3)=[CH:3][CH:4]=2)=[N:9][CH:10]=1)([O-:16])=[O:15]A flask was charged with 2-(4-chlorophenyl)-5-nitropyridine (4.48 g, 14.26 mmol), pinoco boronate (14.48 g, 57.0 mmol), potassium acetate (5.59 g, 57.0 mmol), Pd-(Xphos) (1.404 g, 1.900 mmol), X-phos (1.359 g, 2.85 mmol) and dioxane (50 ml) at room temperature. The flask was sealed, flushed with nitrogen for three times and heated at 115° C. for 72 hours. The mixture was cooled down to room temperature and diluted with dioxane (50 ml) and EtOAc (100 ml), filtered and the filtrate was concentrated. The residue was added dioxane (30 ml) and filtered, the filtrate was purified by flash chromatography (heptanes/acetone 1/2) to afford 5-nitro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (3.9 g, 84%) as yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 1.37 (s, 9H) 7.43-8.15 (m, 7H).
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