Reaction Steps
Using the procedure of Example 9, N-(5,5-diethoxy-1,1,1-trifluoropent-3-yn-2-ylidene)-1,1,1-triphenylmethanamine (2.328 g, 5 mmol), cesium carbonate (4.07 g, 12.50 mmol), 2,2-dimethylpropan-1-amine (1.307 g, 15.00 mmol) and anhydrous DMSO (20 mL) gave 2-(tert-butyl)-6-(diethoxymethyl)-3-fluoro-N-tritylpyridin-4-amine (2.61 g, 97%) as an off-white solid: mp 168-169.5° C.; 1H NMR (400 MHz, CDCl3) δ 7.28 (m, 15H), 6.16 (d, J=6.1 Hz, 1H), 5.71 (d, J=5.2 Hz, 1H), 5.01 (s, 1H), 3.29 (dd, J=9.5, 7.1 Hz, 2H), 3.17 (dq, J=9.4, 7.0 Hz, 2H), 1.36 (d, J=1.3 Hz, 9H), 1.01 (t, J=7.0 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 151.67 (d, J=9.9 Hz), 150.42 (d, J=5.9 Hz), 147.83 (d, J=249.5 Hz), 144.45, 141.00 (d, J=10.3 Hz), 128.91, 128.14, 127.12, 107.63, 102.63, 71.04, 61.35, 36.75 (d, J=5.1 Hz), 29.00 (d, J=3.5 Hz), 15.09; 19F NMR (376 MHz, CDCl3) δ −145.99; HRMS-ESI (m/z) [M+H]+ calcd for C33H37FN2O3, 512.2839. found, 512.2851.
