Benzophenone imine → HCID 86647077, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 mL microwave reaction tube was added N-(5-bromo-2-chloropyridin-3-yl)-N-(methylsulfonyl)methanesulfonamide (Step 0) 1.11 g, 3.04 mmol), xantphos (0.179 g, 0.308 mmol), NaOtBu (1.18 g, 12.3 mmol), Pd2dba3 (0.139 g, 0.152 mmol) and diphenylmethanimine (0.62 mL, 3.7 mmol) in DMF (10 mL). The mixture was degassed by bubbling argon through for 10 min. The tube was heated in Initiator microwave reactor (Biotage) at 120° C. for 30 min. The reaction mixture was partitioned between tris-HCl buffer (1 M, pH 7.0) (80 mL) and EtOAc (50 mL). The aqueous phase was extracted with EtOAc (2×60 mL). The combined organic phases were washed with water (200 mL) and saturated aqueous sodium chloride (150 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 50%) to afford N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)methanesulfonamide (0.90 g, 77% yield) as a light brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.72-7.77 (m, 3H) 7.50-7.56 (m, 1H) 7.43 (t, J=7.53 Hz, 2H) 7.32-7.37 (m, 3H) 7.28-7.31 (m, 1H) 7.11-7.16 (m, 2H) 6.66 (s, 1H) 2.78 (s, 3H).

Provenance & Evidence