Pyridine → HCID 11991895, compound

Participants

Reaction Conditions

Reaction Steps

2-(7-Phenylheptanoyl)oxazole-5-carboxamide (35 mg, 0.117 mmol) was dissolved in 1,4-dioxane (3 mL) and pyridine (2.5 equiv) and trifluoroacetic anhydride (1.3 equiv) were added. The reaction mixture stirred for 2 h at 23° C. The mixture was diluted with CH2Cl2 and the combined organic layers were washed with saturated aqueous NaCl and dried over Na2SO4. Evaporation in vacuo yielded the crude nitrile, which was purified by flash chromatography (2-20% EtOAc/hexanes) to afford the title compound as a clear oil: 1H NMR (CDCl3, 600 MHz) δ 7.84 (s, 1H), 7.28-7.25 (m, 2H), 7.18-7.16 (m, 3H), 3.07 (t, 2H, J=7.8 Hz), 2.60 (t, 2H, J=7.8 Hz), 1.77-1.72 (m, 2H), 1.65-1.60 (m, 2H), 1.41-1.37 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 188.1, 159.5, 143.4, 139.0, 129.3, 129.1, 127.3, 126.5, 109.1, 40.5, 36.7, 32.1, 29.8, 29.7, 24.3; MALDI-FTMS m/z 281.1293 (M+H−, C17H17N2O2, requires 281.1295).

Provenance & Evidence