Benzophenone imine → N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave vial was added N-(5-bromo-2-chloropyridin-3-yl)morpholine-4-sulfonamide (0.500 g, 1.40 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Acros) (0.048 g, 0.084 mmol), tris(dibenzylideneacetone)dipalladium (o) (Strem) (0.015 g, 0.017 mmol), sodium tert-butoxide (Fluka) (0.268 g, 2.8 mmol), toluene (10 mL), and benzophenone imine (Aldrich) (0.260 mL, 1.54 mmol). The resulting mixture was sealed off and microwave heated at 110° C. for 20 min. Reaction mixture was partitioned between EtOAc and Tris HCl 1M pH7. 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 (24 g, 10% to 20% EtOAc in hexanes) to afford the desired product as a yellow foam (150.0 mg). MS (ESI pos. ion) m/z: 457.0. 1H NMR (300 MHz, CDCl3) δ ppm 3.07 (d, J=4.38 Hz, 4H) 3.63 (d, J=4.38 Hz, 4H) 6.62 (br. s., 1H) 7.14 (d, J=3.95 Hz, 2H) 7.35 (d, J=5.85 Hz, 4H) 7.40-7.49 (m, 2H) 7.49-7.58 (m, 1H) 7.63 (s, 1H) 7.74 (d, J=7.16 Hz, 2H).

Provenance & Evidence