Chlorotrimethylsilane → 6-Benzyl-3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridine

Participants

Reaction Conditions

Reaction Steps

To a flame-dried flash under nitrogen was added Rieke zinc (2.3 mL, 1.75 mmol). The total volume of the reaction was brought to 5 mL using dry THF. To the slurry was added dibromoethane (10.0 μL, 0.01 mmol), and the reaction warmed to 65° C. for 3 minutes. The reaction was then cooled to 35° C., and chlorotrimethylsilane (30.0 μL, 0.25 mmol) added, and the resulting reaction stirred for 30 minutes at 35° C. Benzyl bromide (55 uL, 0.46 mmol), was added and the reaction stirred a further 30 minutes at 35° C. To the mixture was then added 6-bromo-3-(2-chloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine (136 mg, 0.44 mmol) and Pd(PPh3)4 and the temperature increased to 50° C. Flash chromatography purification (elution with 35-85% ethyl acetate/hexane), followed by preparatory HPLC (15-80% water/acetonitrile) of the crude reaction mixture yielded the title compound (10 mg, 7%). MS (M+1)=320.4.

Provenance & Evidence