(NE)-2-methyl-N-[[4-(9-phenyl-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)phenyl]methylidene]propane-2-sulfinamide → 2-Methyl-N-{1-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethyl}propane-2-sulfinamide

Participants

Reaction Steps

Methylmagnesium bromide solution (13.5 mL of 1.4 M solution in 3:1 toluene/THF, 19 mmol) was added to a stirred solution of 2-methyl-N-{(1E)-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methylidene}propane-2-sulfinamide (7-2, 298 mg, 0.66 mmol) in methylene chloride (5 mL) at −78° C. and the solution was warmed to rt. After 18 h, the reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give an amber foam, which was purified via silica gel chromatography (0-10% MeOH/CH2Cl2 over 30 min) to give the title compound as a yellow foam.

Provenance & Evidence