Pyridine → HCID 11254965, compound

Participants

Reaction Steps

3-Methoxycarbonylphenylboronic acid was subjected to similar coupling procedures with NHP as outlined above (method 1). A 100 mL round bottom flask was charged with N-hydroxyphthalimide (2.19 g, 13.4 mmol), copper (I) chloride (1.34 g, 13.5 mmol), freshly activated 4 Å molecular sieves (˜5 g), and 3-methoxycarbonylphenylboronic acid (4.79 g, 26.6 mmol). 1,2-Dichloroethane (60 mL) was added followed by pyridine (1.20 mL, 14.8 mmol), and the reaction suspension was stirred in an air atmosphere at room temperature. After 4 days, the mixture was adsorbed onto silica gel and concentrated to a powder. Flash chromatographic purification over silica (33-50% gradient EtOAc in hexanes) afforded 13 as a white solid (1.85 g, 46%). 1H-NMR (500 MHz, CDCl3) δ 3.90 (s, 3H), 7.38-7.41 (ddd, J=1.0, 2.5, 8.3 Hz, 1H), 7.44 (t, J=8.3 Hz, 1H), 7.78 (dd, J=1.0, 2.5 Hz, 1H), 7.82-7.86 (m, 3H), 7.92-7.96 (m, 2H); 13C-NMR (125 MHz, CDCl3) δ 52.5, 115.0, 119.3, 124.3, 125.9, 129.0, 130.0, 132.1, 135.2, 159.0, 163.0, 166.2; ESI-MS 298 m/z [MH]+, C16H12NO5 requires 298.

Provenance & Evidence