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-1271b06bb0894d8488ee6781e825921f

Quelldatensatz

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06288092B1