Ammonium Chloride → 3-(4-Methylphenyl)pyridine-2-carbonitrile

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Reaction Steps

To a mixture of p-tolylmagnesium bromide (9.3 mL of a 1M solution in Et2O, 9.28 mmol) in THF (17 mL) at -78° C. was added ZnCl2 (9.3 mL of a 1M solution in Et2O, 9.28 mmol). The resulting slurry was warmed to rt for 20 min then cooled to 0° C. Bis-(triphenylphosphine)nickle(II) chloride (178 mg, 0.27 mmol) and 3-bromo-2-cyanopyridine (1.0 g, 5.5 mmol); (prepared as reported: Chem. Pharm Bull., 1985, vol. 33, p 565) were added in one portion. After 1 h, saturated aqueous NH4Cl (50 mL) was added and the mixture was extracted with EtOAc (2×50 mL). Purification by flash chromatography (40% EtOAc/hexanes) gave the above titled compound as a white solid.

Provenance & Evidence