HCID 23156952, compound → HCID 23156957, compound

A mixture of 2 (2.48 g, 10 mmol), 2-tributyltin furan (3.58 g, 10 mmol), and tetrakis(triphenylphosphine) palladium (200 mg) in dry dioxane (60 mL) was heated under nitrogen at reflux (100-110° C.) for 24 h. The solvent was evaporated under reduced pressure and the resulting solid was dissolved in ethyl acetate. This solution was passed through celite to remove Pd. The solution was evaporated, and the solid was collected via filtration and washed with hexanes to furnish compound 3 in 79.5% yield, mp 104-105° C. 1H NMR (CDCl3); δ 6.51 (dd, J=3.6 Hz, J=1.8 Hz, 1H), 6.68 (m, 2H), 6.87 (d, J=3.6 Hz, 1H), 7.46 (d, J=1.8 Hz, 1H), 7.66 (d, J=8.4 Hz, 2H), 7.77 (d, J=8.4 Hz, 2H). 13C NMR (CDCl3); δ 150.9, 147.5, 145.8, 142.4, 134.1, 132.5, 123.7, 118.9, 111.6, 110.1, 107.5, 106.3. EIMS (m/z, rel.int.); 235 (M+, 100), 206 (10), 178 (15). Calcd for C15H9NO2: C, 76.59; H, 3.86; N, 5.95. Found. C, 76.35; H, 3.88; N, 5.92.