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

Temperature

90 °C

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]+.

1. customwas purged for 10 min with argon
2. temperatureCooled to ambient temperature
3. concentrationthe reaction mixture was concentrated
4. additionpoured onto water (300 mL)
5. extractionextracted with ethyl acetate (3×500 mL)
6. washThe combined organic layers were washed with water (300 mL) and brine (2×250 mL)
7. dry with materialdried over magnesium sulfate
8. concentrationConcentration
9. waitleft a dark brown residue which
10. customwas purified by flash chromatography with n-heptane and acetone

ORD record

ord-997445f3d77c4365a31c5f1788037fee

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544704B2