Ethyl 4-(6-oxo-1,6-dihydropyridin-3-yl)benzoate → HCID 18617476, compound

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Reaction Steps

Ethyl 4-(6-oxo-1,6-dihydro-pyridin-3-yl)-benzoate (450 mg, 1.8 mmol) (reference example 36f) is dissolved in HOAc (15 mL), and the the solution is degassed several times by alternating N2/vacuum. 50 mg of PtO2 is added and the mixture is degassed for several minutes before being placed under a H2 atmosphere. The mixture is stirred at room temperature for 9 hours then degassed several times by alternating N2/vacuum then filtered through a plug of celite. The plug is washed thoroughly with HOAc and the filtrate concentrated. The residue is chromatographed first on silica gel (3% MeOH/CH2Cl2), and then by Reverse-Phase HPLC to afford 330 mg of the title compound (72%) as a white solid. 1H NMR (CDCl3) δ 1.39 (t, J=7 Hz, 3H), 2.12 (m, 2H), 2.56 (m, 2H), 3.13 (m, 1H), 3.41 (dd, J=11.3, 11.3, 1H), 3.53 (m, 1H), 4.37 (q, J=7, 2H), 6.78 (bs, 1H), 7.16 (d, J=8 Hz, 2H), 8.01 (d, J=8 Hz, 2H). MS (Ion spray) m/z 248 (M+H)+.

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