2-Aminopyridine → 2-(5-Bromopyrid-2-yl)-N-pyrid-2-ylacetamide

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Reaction Steps

Under an inert atmosphere, 0.09 g (0.95 mmol) of 2-aminopyridine, 0.31 g (2.4 mmol) of diisopropylethylamine and 0.35 g (1.1 mmol) of TBTU are successively added to 0.26 g (0.95 mmol) of (5-bromo-2-pyridyl)acetic acid (a synthesis of which is described in Tetrahedron, 1997, 53(24) 8257-8268 Gurnos J. et al.) dissolved in anhydrous THF (4 ml). The reaction mixture is stirred for 3 hours at room temperature. The reaction mixture is concentrated under reduced pressure, the residue is taken up in ethyl acetate (20 ml) and the organic phase thus obtained is then washed with saturated ammonium chloride solution (15 ml) and with saturated sodium hydrogen carbonate solution (15 ml), and then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/ethyl acetate, 1% NH4OH), with a gradient of 0% to 20% ethyl acetate, 1% NH4OH. 0.125 g of compound is obtained in the form of a white powder. Yield: 45%. Melting point: 131° C. MH+: 292-294 (tr: 6.1 min., condition 1).

Provenance & Evidence