N-(2-Fluoro-4-iodophenyl)methanesulfonamide → N-(4-Cyano-2-fluorophenyl)methanesulfonamide

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A mixture of Example 10A (5.0 g, 16 mmol), dicyanozinc (1.12 g, 9.5 mmol), and Pd(PPh3)4 (0.92 g, 0.79 mmol) in DMF (15 mL) was heated at 80° C. overnight. The mixture was concentrated in vacuo then diluted with EtOAc (400 mL) and washed with brine (3×100 mL). The organic extract was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography (SiO2, 25-50% Hexanes/EtOAc gradient) to afford the title compound (3.4 g, 99% yield). 1H NMR (300 MHz, DMSO-d6) δ 10.28 (s, 1H), 7.92 (dd, J=10.7, 1.8 Hz, 1H), 7.73-7.56 (m, 2H), 3.31 (s, 3H). MS (ESI; M−H) m/z 213.

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