Water → 1-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-one

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Reaction Steps

To a stirring solution of the enol silyl ether from step 2 (100.0 g, 322 mmol) and allyl methyl carbonate (43.6 g, 386 mmol) in DMSO (625 ml) at ambient temperature is added Pd(OAc)2 (7.20 g, 32 mmol). The resulting solution is stirred under N2 at ambient temperature overnight. H2O (1 liter) is added and solvent allowed to cool to ambient temperature. The aqueous layer is extracted with EtOAc (2×800 ml) and the organic layers combined, washed with brine (800 ml) and organics dried over MgSO4. The solvent is removed and residue recrystallized from EtOAc/MTBE to afford 53.6 g (70%) of the title compound as a yellow solid. 1H NMR (CDCl3) δ 2.71 (m, 2 H), 4.06 (m, 2 H), 5.41 (d, J=8 Hz, 1 H), 7.25 (m, 1 H), 7.35 (d, J=8 Hz, 1 H), 8.08 (m, 2 H); Anal. Calcd for C11H9FN2O3: C, 55.94; H, 3.84; N, 11.86; F, 8.04. Found: C, 55.82; H, 3.81; N, 11.67.

Provenance & Evidence