Triethylamine → Methyl 2-(4-fluoro-2-((trimethylsilyl)ethynyl)phenyl)acetate

Participants

Reaction Steps

To a solution of ester 325 (3.80 g, 12.9 mmol) in dry DME (100 mL) at 0° C. was added triethylamine (4.5 mL, 3.3 g, 33 mmol), copper (I) iodide (0.50 g, 2.6 mmol), and bis(triphenylphosphine) palladium (II) chloride (0.38 g, 0.54 mmol). The mixture was degassed with a stream of N2 for 5 min, then trimethylsilylacetylene (4.0 mL, 2.8 g, 29 mmol) was added and the reaction mixture was warmed to room temperature and stirred for 3 h. It was then concentrated under reduced pressure, re-dissolved in ether, filtered and concentrated. Silica gel chromatography of the residue (eluent 10% ethyl acetate/hexanes) afforded 326 (3.30 g, 97% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.23 (dd, J=8.6, 5.7 Hz, 1H); 7.14 (dd, J=9.0, 2.7 Hz, 1H); 7.00 (dt, J=8.4, 2.7 Hz, 1H); 3.79 (s, 2H); 3.70 (s, 3H); 0.25 (s, 9H). LCMS: (M+H) 265.2.

Provenance & Evidence