Triethylamine → 5-(2-(Trimethylsilyl)ethynyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-5-bromopyridine (50.0 g, 289 mmol), trimethylsilylacetylene (112 mL, 809 mmol), triethylamine (120 mL, 867 mmol), PdCl2(PPh3)2 (4.06 g, 5.78 mmol) and PPh3 (1.52 g, 5.78 mmol) in DMF (290 mL) was purged for 10 min with argon. Then cuprous iodide (340 mg, 2.89 mmol) was added and the reaction mixture was heated up to 90° C., stirring was continued at 90° C. for 4.5 h. Cooled to ambient temperature, the reaction mixture was concentrated, poured onto water (300 mL) and extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with water (300 mL) and brine (2×250 mL) and dried over magnesium sulfate. Concentration left a dark brown residue which was purified by flash chromatography with n-heptane and acetone to give the title compound as a brown solid (41.7 g, 76%). MS: m/e=191.2 [M+H]+.

Provenance & Evidence