Acetic Acid → (E)-N-benzyl-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}amine

Participants

Reaction Steps

(E)-2-[2-(1H-indazol-3-yl)vinyl]phenylamine (60 mg, 0.26 mmol) was dissolved in dichloroethane and the solution was added with benzaldehyde (28 μL, 0.28 mmol), sodium triacetoxyborohydride (81 mg, 0.38 mmol) and acetic acid (15 mL, 0.25 mmol), followed by stirring at room temperature for 13 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. A crude product was purified by silica gel chromatography [ethyl acetate/hexane=1/8 to 1/1] and further crystallized from ethyl acetate to obtain Compound 26 (31.1 mg, 38%).

Provenance & Evidence