Sodium hydride → 4-bromo-N-((4-chlorophenylamino)(2,6-difluorophenyl)methyl)benzamide

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4-Bromobenzamide 117 (0.94 g, 4.56 mmol) and 18-crown-6 (1.2 g, 4.54 mmol) in DMF (6 mL) was treated with sodium hydride (0.37 g, 9.25 mmol) for 5 minutes at room temperature. 4-Chloro-N-(2,6-difluorobenzylidene)aniline 116 (0.936 g, 3.72 mmol) in DMF (4 mL) was added and the mixture was heated to 50° C. for 5 minutes. The reaction mixture was quenched with crushed ice and the product was isolated by a typical aqueous workup and extraction with ethyl acetate. Chromatographic purification (9:1 hexanes:ethyl acetate) followed by trituration (ethanol) of the material gave 4-bromo-N-((4-chlorophenylamino)(2,6-difluorophenyl)methyl)benzamide (Compound-6) as a white solid (292 mg, 17%). 1H NMR (300 MHz, CDCl3): δ=7.62-7.52 (series m, 4H), 7.38-7.28 (m, 1H), 7.19-7.15 (m, 2H), 7.14-7.08 (m, 1H), 7.02-6.96 (m, 2H), 6.88-6.85 (m, 1H), 6.76-6.72 (m, 2H).

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