[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].O.[C:24](#[N:26])[CH3:25]>>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:25][C:24]#[N:26])[CH:10]=2)[O:3]1A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.50 g, 2.58 mmol), sodium iodide (39 mg, 0.26 mmol) bromoacetonitrile (1.3 g, 10.8 mmol) and potassium carbonate (1.0 g, 7.8 mmol) in acetonitrile (10 mL) was heated at 70° C. overnight. Water was added and the solution was extracted with EtOAc (3×). The organic was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (10% to 100% EtOAc/hexane) to obtain 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetonitrile (0.38 g, 63% yield). MS (ESI) m/z: 234.1 (M+H+).
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