Dimethyl Sulfide → 3-Methylsulfanyl-5-phenylethynylpyridine

Participants

Reaction Steps

Add a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran (0.96 mL, 1.94 mmol) to a solution of 3-bromo-5-phenylethynylpyridine, (prepared as described in EXAMPLE 9), (500 mg, 1.94 mmol) in anhydrous tetrahydrofuran (2 mL) and stir under nitrogen at room temperature for 2 h. Add triethylamine (0.27 mL, 1.94 mmol) and dimethyl sulfide (0.175 mL, 1.94 mmol). Stir for an additional 2 h, dilute with water, extract with dichloromethane, dry (magnesium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting from 100:0 to 100:50 with hexanes:ethyl acetate, to give the title compound (10.1 mg, 2.3%).

Provenance & Evidence