Reaction Steps
Using the procedure of Example 9, N-(5,5-diethoxy-1,1,1-trifluoropent-3-yn-2-ylidene)-1,1,1-triphenylmethanamine (4.66 g, 10 mmol), 2-(4-fluorophenyl)ethanamine (1.670 g, 12.00 mmol), cesium carbonate (8.15 g, 25.00 mmol) and DMSO (30 mL) gave 6-(diethoxymethyl)-3-fluoro-2-(4-fluorobenzyl)-N-tritylpyridin-4-amine (3.25 g, 56.4%) as a yellow glass, which crystallized from CH3CN (25 mL): mp 129-130° C.; 1H NMR (400 MHz, CDCl3) δ 7.27 (m, 19H), 6.94 (m, 2H), 6.19 (d, J=6.6 Hz, 1H), 5.71 (d, J=4.3 Hz, 1H), 5.06 (s, 1H), 4.05 (d, J=2.9 Hz, 2H), 3.23 (dq, J=9.4, 7.1 Hz, 2H), 3.13 (dq, J=9.4, 7.0 Hz, 2H), 1.00 (t, J=7.0 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 161.48 (d, J=243.8 Hz), 152.10 (d, J=5.9 Hz), 147.04 (d, J=246.0 Hz), 144.65 (d, J=13.9 Hz), 144.13, 140.88 (d, J=9.4 Hz), 134.69 (d, J=3.1 Hz), 130.28 (d, J=7.8 Hz), 128.86, 128.20, 127.24, 114.99 (d, J=21.2 Hz), 108.23, 101.87, 71.24, 61.05, 37.45, 15.05; 19F NMR (376 MHz, CDCl3) δ−117.27, −151.26 (dd, J=6.6, 3.6 Hz); HRMS-ESI (m/z) [M+H]+ calcd for C36H34F2N2O2, 564.2588. found, 564.2595.
