Triethylamine → N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorobenzyl]acetamide

Participants

Reaction Conditions

Reaction Steps

Add zinc (II) bromide (313 mg, 1.20 mmol), triethylamine (0.67 mL, 4.80 mmol), 5-bromonicotinonitrile (183 mg, 1.00 mmol), tetrakis(triphenylphosphine)palladium (0) (58 mg, 0.050 mmol), and a 1.0 M solution of tetrabutylammonium fluoride (2.0 mL) in tetrahydrofuran to a solution of N-(2-fluoro-5-trimethylsilanylethynylbenzyl) -acetamide, (prepared as described in PREPARATION 31), (289 mg, 1.10 mmol) in anhydrous tetrahydrofuran (2.5 mL) under nitrogen. Heat to 60° C. for 5 h, cool to room temperature, and filter through diatomaceous earth. Concentrate and purify the residue by silica gel chromatography, eluting with 100:0 to 50:50 hexanes:ethyl acetate, to give the title compound as a white crystalline solid (122 mg, 42%).

Provenance & Evidence