2,6-Dibromopyridine → 2-(6-Bromopyridin-2-yl)benzonitrile

Temperatur

80 °C

A mixture of 2,6-dibromopyridine (2.07 g, 8.7 mmol), 2-(4,4,5,5-tetramethyl[1,3,2]-dioxaborolan-2-yl)benzonitrile (prepared as described in Tetrahedron (2001), 57(49), 9813-9816, 3.00 g, 13 mmol) and potassium phosphate (3.71 g, 17 mmol) in DMF (40 mL) was degassed with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (303 mg, 0.26 mmol) was added, the mixture was degassed as before, and was then stirred at 80° C. under nitrogen overnight. The mixture was partitioned between water and ethyl acetate, and the resulting aqueous layer was washed with ethyl acetate (2×100 mL). The combined organic layers were washed with water (1×100 mL) and saturated sodium chloride solution (1×100 mL), then were dried over magnesium sulfate and concentrated in vacuo. The residual material was purified by flash chromatography on silica gel, eluting with 50% ethyl acetate in isohexane, affording 2-(6-bromopyridin-2-yl)benzonitrile as a solid (680 mg, 30%). δH (400 MHz, CDCl3) 7.51-7.57 (2H, m), 7.68-7.73 (2H, m), 7.80 (2H, d, J 7.7), 7.91 (1H, dd, J 0.7 and 7.7).

1. customwas degassed with nitrogen
2. customthe mixture was degassed as before, and
3. customThe mixture was partitioned between water and ethyl acetate
4. washthe resulting aqueous layer was washed with ethyl acetate (2×100 mL)
5. washThe combined organic layers were washed with water (1×100 mL) and saturated sodium chloride solution (1×100 mL)
6. dry with materialwere dried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. customThe residual material was purified by flash chromatography on silica gel
9. washeluting with 50% ethyl acetate in isohexane

ORD-Eintrag

ord-5c65db8f744549f98e37bbf5bba44eed

Quelldatensatz

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06960598B2