2-Bromopyridine → 2-(3-Bromophenyl)pyridine

A mixture of 2-bromopyridine (4.8 g, 30.33 mmol), 3-bromophenyl boronic acid (4.06 g, 20.22 mmol), glyme (35 mL), tetrakis(triphenylphosphine)palladium(0) (0.4 g) and a solution of potassium carbonate (7.6 g, 55 mmol) in water (35 mL) was stirred well at reflux under nitrogen overnight. After cooling, the reaction mixture was diluted with ethyl acetate (600 mL) and washed with water (3×200 mL). The solvent and excess 2-bromopyridine were removed on a rotary evaporator (bath temperature=75° C.) and the crude product was purified by chromatography on silica (110 g) with 2% ethyl acetate in heptane (6 L) to produce 1 (3.55 g, 75%).

1. temperatureat reflux under nitrogen overnight
2. temperatureAfter cooling
3. washwashed with water (3×200 mL)
4. customThe solvent and excess 2-bromopyridine were removed on a rotary evaporator (bath temperature=75° C.)
5. customthe crude product was purified by chromatography on silica (110 g) with 2% ethyl acetate in heptane (6 L)

ORD record

ord-7c1a895424ee4f9aa5b900cf7094252a

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541522B2