2,6-Dichloropyridine → 4-Chloro-2-[(6-chloro-2-pyridinyl)amino]benzonitrile

Temperature

112 °C

A mixture of 2,6-dichloropyridine (2 g, 13.51 mmol), 2-amino-4-chlorobenzonitrile (2.062 g, 13.51 mmol), PALLADIUM(II) ACETATE (0.303 g, 1.35 mmol), BINAP (1.683 g, 2.70 mmol) and potassium carbonate (5.60 g, 40.54 mmol) in toluene (100 mL) was stirred at reflux under N2 for 5hrs. LCMS detected major peak as desire product. The resulting suspension was cooled, filtered, and the filtrate was concentrated under reduced pressure. Column chromatography of the residue on silica gel using 15% to 20% ethyl acetate in hexane, then 100% ethyl acetate as eluent gave the crude product which was recrystallized from methanol/DCM to yield a light yellow solid as desired product 4-chloro-2-(6-chloropyridin-2-ylamino)benzonitrile (3.34 g, 93 %)

ORD record

ord-9455bd6f5eee4a2d8aef36cf7b2f19e8

Source dataset

750 AstraZeneca ELN dataset

Original link

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