Benzophenone imine → HCID 86647084, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave vial was added N-(5-bromo-2-chloropyridin-3-yl)-N-(cyclopropylsulfonyl)cyclopropanesulfonamide (0.880 g, 2.117 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Acros) (0.122 g, 0.212 mmol), tris(dibenzylideneacetone)dipalladium (0) (Strem) (0.097 g, 0.106 mmol), sodium tert-butoxide (Fluka) (0.814 g, 8.47 mmol), DMF (10 mL), and benzophenone imine (Aldrich) (0.426 mL, 2.54 mmol). The resulting mixture was degassed by bubbling N2 for 5 min. It was sealed off and microwave heated at 130° C. for 20 min. The resulting mixture was partitioned between EtOAc and sat. NH4Cl (25 mL). 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 (80 g, 10% to 20% acetone in hexanes) to afford the desired product as a yellow foam-like solid (300 mg). MS (ESI pos. ion) m/z: 412.0. 1H NMR (300 MHz, CDCl3) δ ppm 0.89 (d, J=7.02 Hz, 2H) 1.03 (d, J=3.07 Hz, 2H) 6.60 (br. s., 1H) 7.14 (d, J=3.65 Hz, 2H) 7.34 (d, J=6.28 Hz, 4H) 7.39-7.48 (m, 2H) 7.49-7.56 (m, 1H) 7.68-7.80 (m, 3H).

Provenance & Evidence