Sodium Carbonate → 4-[4-Methoxy-3-(phenyl)phenyl]pyridine

Temperatur

80 °C

A stirred mixture of 3-bromobenzonitrile (0.91 g, 5.0 mmol), 2-Methoxy-5-(pyridin-4-yl)phenylboronic acid (0.50 g, 2.3 mmol), tri-o-tolylphosphine (0.152 g, 0.50 mmol), palladium (II) acetate (0.056 g, 0.25 mmol), sodium carbonate (1.59 g, 15 mmol) and water (15 mL) in dimethylformamide (46 mL) is heated at 80° C. for 5 h. The mixture is then treated with water (100 mL) and extracted with ethyl acetate (3×80 mL). The combined extracts are dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by chromatography (silica gel, ethyl acetate) to give 4-[4-methoxy-3-(phenyl)phenyl]pyridine base. The base is dissolved in diethylether (5 mL), treated with methanolic HCl (excess), evaporated to dryness under reduced pressure and recrystallised from ethanol-ether to give 4-[2-methoxy-3′-cyano-biphenyl-5-yl]pyridine, hydrochloride as a pale-yellow crystalline solid, m.p. 142-150° C.

1. extractionextracted with ethyl acetate (3×80 mL)
2. dry with materialThe combined extracts are dried (Na2SO4)
3. filtrationfiltered
4. customthe solvent is evaporated off under reduced pressure
5. customto yield the crude product which
6. customis purified by chromatography (silica gel, ethyl acetate)

ORD-Eintrag

ord-3d730bd8e19749e6b02cb3efe81bf952

Quelldatensatz

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06410547B1