Benzophenone imine → N-(5-(Diphenylmethyleneamino)-2-methylpyridin-3-YL)methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To two 20 mL microwave vials were added N-(5-bromo-2-methylpyridin-3-yl)-N-(methylsulfonyl)methanesulfonamide (1.300 g, 3.79 mmol) (780 mg each), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Acros) (0.219 g, 0.379 mmol) (121 mg each), tris(dibenzylideneacetone)dipalladium (o) (Strem) (0.173 g, 0.189 mmol) (104 mg each), sodium tert-butoxide (Fluka) (1.092 g, 11.36 mmol) (655 mg), DMF (12 mL each vial), and benzophenone imine (Aldrich) (0.699 mL, 4.17 mmol) (0.420 mL each). Both resulting mixtures were degassed by bubbling N2 for 5 min then sealed off and microwave heated at 130° C. for 20 min. LC/MS showed no sign of starting material mass with desired product mass as the major peak on both vials. Both reaction mixtures were combined and partitioned between EtOAc and sat. NH4Cl. The aqueous layer was extracted with EtOAc (2×15 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (120 g, 20% to 40% acetone in hexanes) to afford the desired product as a yellow foam-like solid (430 mg). MS (ESI pos. ion) m/z: 365.8. 1H NMR (300 MHz, CDCl3) δ ppm 2.43 (s, 3H) 2.75 (s, 3H) 6.07 (br. s., 1H) 7.09-7.21 (m, 3H) 7.29-7.37 (m, 3H) 7.38-7.47 (m, 2H) 7.48-7.56 (m, 1H) 7.75 (d, J=7.02 Hz, 2H) 7.92 (d, J=2.19 Hz, 1H).

Provenance & Evidence