Triethylamine → (4-Acetoxy-6-fluoro-3-trimethylsilanylethynyl-naphthalen-2-yl)-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-acetoxy-6-fluoro-3-iodo-naphthalen-2-yl)acetic acid methyl ester (300 mg, 0.75 mmol) and triethylamine (3 mL) in N,N-dimethylformamide (3 mL), was added bis(triphenylphosphine)dichloropalladium(II) (53 mg, 0.075 mmol), copper iodide (42 mg, 0.229 mmol) and trimethylsilanylacetylene (108 mg, 1.12 mmol) under an argon atmosphere. After being heated at 150° C. for 6 minutes with microwave irradiation, the resulting mixture was cooled, diluted with ethyl acetate (20 mL), and washed with brine (15 mL×2). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column (elution with 10% ethyl acetate in petroleum ether) to afford (4-acetoxy-6-fluoro-3-trimethylsilanylethynyl-naphthalen-2-yl)-acetic acid methyl ester (208 mg, 75%) as a light yellow solid.

Provenance & Evidence