4-Fluorophenylboronic acid → N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(4-fluorophenyl)-1-isopropyl-3-methyl-1H-indazole-4-carboxamide

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In a 25 mL sealable tube under nitrogen were combined 6-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-1H-indazole-4-carboxamide (90 mg, 0.21 mmol), (4-fluorophenyl)boronic acid (43.8 mg, 0.31 mmol) in dioxane/water (3 mL:1 mL). PdCl2(dppf)-CH2Cl2 adduct (5.11 mg, 0.006 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. Sodium bicarbonate (52.6 mg, 0.63 mmol) was added, the vessel was sealed, and the insoluble mixture was heated in a microwave at 100° C. for 20 min. The mixture was evaporated, DCM/MeOH (1:1) was added, the contents pre-absorbed on silica gel and purified by SiO2 chromatography (eluent: gradient 0 to 80:20:2 DCM/MeOH/NH4OH). The collected product was suspended in EtOAc along with some hexanes. The mixture was sonicated, and the solids that precipitated were filtered and dried to afford the title compound as a white solid (73 mg, 77%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.50 (s, 1H) 8.46 (t, J=5.05 Hz, 1H) 7.94 (d, J=1.26 Hz, 1H) 7.83-7.88 (m, 2H) 7.31-7.36 (m, 3H) 5.88 (s, 1H) 5.06 (quin, J=6.63 Hz, 1H) 4.38 (s, 1H) 4.36 (s, 1H) 2.43 (s, 3H) 2.24 (s, 3H) 2.12 (s, 3H) 1.47 (s, 3H) 1.45 (s, 3H). LC-MS (ES) m/z=446.9

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