Benzophenone imine → N-(5-(diphenylmethyleneamino)-2-methoxypyridin-3-yl)methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a 5 mL microwave reaction tube was added N-(5-bromo-2-methoxypyridin-3-yl)methanesulfonamide (0.208 g, 0.739 mmol), xantphos (Acros, 0.044 g, 0.077 mmol), Pd2dba3 (Aldrich, 0.034 g, 0.037 mmol), NaOtBu (Aldrich, 0.178 g, 1.85 mmol) and diphenylmethanimine (Aldrich, 0.130 mL, 0.776 mmol) in DMF (3 mL). The mixture was degassed by bubbling argon through for 5 min. The tube was heated in a microwave reactor (Biotage) at 120° C. for 30 min. The reaction mixture was partitioned between tris-HCl buffer (1 M, pH 7.0) (20 mL) and EtOAc (10 mL). The aqueous phase was extracted with EtOAc (20 mL). The combined organic phases were washed with saturated aqueous sodium chloride (20 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (50 g, eluent: EtOAc in hexanes 20% to 80%) to afford N-(5-(diphenylmethyleneamino)-2-methoxypyridin-3-yl)methanesulfonamide (0.109 g, 39% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.69-7.74 (m, 2H) 7.53 (d, J=2.35 Hz, 1H) 7.46-7.51 (m, 1H) 7.38-7.44 (m, 2H) 7.30-7.36 (m, 3H) 7.12-7.18 (m, 3H) 6.60 (s, 1H) 3.94 (s, 3H) 2.69 (s, 3H).

Provenance & Evidence