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

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave reaction tube was added N-(5-bromo-2-chloropyridin-3-yl)morpholine-4-sulfonamide (Example 366, Step 3) 0.510 g, 1.43 mmol), xantphos (0.0839 g, 0.145 mmol), Pd2dba3 (0.0646 g, 0.071 mmol), NaOtBu (Aldrich, 0.418 g, 4.35 mmol) and diphenylmethanimine (Aldrich, 0.264 mL, 1.57 mmol) in DMF (6 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 saturated aqueous ammonium chloride (40 mL) and EtOAc (40 mL). The aqueous phase was extracted with EtOAc (2×40 mL). The combined organic phases were washed with water (80 mL) and saturated aqueous sodium chloride (80 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (100 g, eluent: EtOAc in hexanes 0% to 70%) to afford N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-sulfonamide in 2 fractions (total 0.42 g, 72% yield) as a yellow solid (0.26 g) and a light brown solid (0.21 g). 1H NMR (400 MHz, CDCl3) δ ppm 7.73 (d, J=7.43 Hz, 2H) 7.62 (d, J=2.35 Hz, 1H) 7.49-7.55 (m, 1H) 7.43 (t, J=7.53 Hz, 2H) 7.31-7.37 (m, 4H) 7.11-7.16 (m, 2H) 6.63 (br. s., 1H) 3.60-3.65 (m, 4H) 3.03-3.09 (m, 4H).

Provenance & Evidence