2,4-Dichloropyridine → N-(4-chloro-2-pyridinyl)-1,3-oxazol-2-amine

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To a flask containing 2,4-dichloropyridine (0.109 mL, 1.01 mmol), sodium phenolate (177 mg, 1.52 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (11.60 mg, 0.01 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (17.59 mg, 0.03 mmol) (Xantphos), was added degassed dioxane (4 mL) and the mixture allowed to stir under nitrogen atmosphere for 5 min. To this solution was added oxazol-2-amine (94 mg, 1.11 mmol) and the reaction mixture was heated to 80 °C for three hours. A 1H NMR was measured of the crude reaction after the solvent had been removed. **This indicated the presence of significant amounts of 2,4-dichloropyridine as well as 2-amino oxazole**. LCMS of the crude reaction mixture at t= 90 min and at t= 3 h showed the desired product was present. The crude reaction mixture was dry loaded without workup and purified by automated flash chromatography.

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