2-Chloro-3-nitropyridine → HCID 89760889, compound

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Reaction Steps

A dry, argon-filled Schlenk tube with a magnetic stirrer bar and septum is initially charged with (TMP)2Zn.MgCl2 (3.16 ml, 1.2 mmol). After adding 2-chloro-3-nitropyridine (159 mg, 1 mmol) in anhydrous THF (2 ml) at 25° C., the mixture is stirred for 1 min, then a solution of ethyl 4-iodobenzoate (387 mg, 1.4 mmol), bis(dibenzylideneacetone)palladium(0) (17 mg, 3 mol %) and tri-2-furylphosphine (14 mg, 6 mol %) in anhydrous THF (2 ml) is added dropwise and the mixture is stirred at 25° C. for 1 h. For workup, the mixture is diluted with aqueous sat. NH4Cl solution (30 ml) and extracted with ethyl acetate (3×30 ml). After the combined organic phases have been dried over Na2SO4, the solvent has been distilled off and purification has been effected by column chromatography on silica gel (heptane:ethyl acetate), the desired compound (177 mg, 58% of theory) was obtained as a yellowish oil.

Provenance & Evidence