Benzophenone imine → N-(2-Chloro-5-(diphenylmethyleneamino)pyridin-3-YL)-4-fluorobenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(5-bromo-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide (Inogent, Inc.) (1.000 g, 2.74 mmol), palladium (II) acetate (Aldrich) (0.035 g, 0.156 mmol), (diphenylphosphino)xanthene (Acros) (0.176 g, 0.304 mmol), sodium tert-butoxide (Fluka) (0.620 g, 6.45 mmol), toluene (10 mL), and benzophenone imine (Aldrich) (0.459 mL, 2.74 mmol) was heated at 100° C. in a sealed tube for 6 h. The reaction mixture was partitioned between EtOAc and Tris HCl (1 M, pH 7). The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (120 g, 10% to 20% acetone in hexanes) to give the product as a yellow solid (0.520 g). m/z (ESI, +ve ion) 466.0 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 7.75 (d, J=7.45 Hz, 2H); 7.61 (d, J=2.05 Hz, 1H); 7.50-7.59 (m, 3H); 7.40-7.49 (m, 3H); 7.35 (br. s., 3H); 7.03-7.17 (m, 4H); 6.73 (br. s., 1H).

Provenance & Evidence