Reaction Steps
To a solution of trifluoro-methanesulfonic acid 6-acetyl-quinolin-4-yl ester (321.7 mg, 1.008 mmol) and (2-butoxy-3,5-diisopropyl-phenyl)-boronic acid (315.3 mg, 1.133 mmol) (see Example 17, step B) in toluene (10 mL) was added 2N Na2CO3 (1.1 mL) and Pd(PPh3)4 (117.1 mg, 0.101 mmol). The solution was stirred at 80° C. for 2 h under N2 atm. The mixture was poured into brine (30 mL) and extracted with ethyl acetate (30 mL). The organic phase was dried, filtered, and concentrated. The crude material was purified by flash chromatography (2:8) ethyl acetate:hexanes to give 1-[4-(2-butoxy-3,5-diisopropyl-phenyl)quinolin-6-yl]-ethanone (378 mg, 93% yield) as a light yellow crystalline solid. Mp 132.8° C. 1H NMR (400 MHz, DMSO-d6): δ 9.01 (d, 1H, J=4.4), 8.40 (d, 1H, J=2.0), 8.25 (2d, 1H, J=2.0, 8.8), 8.16 (d, 1H, J=8.8), 7.50 (d, 1H, J=4.4), 7.24 (m, 1H), 7.00 (d, 1H, J=2.4),3.36 (m, 1H), 3.26 (m, 1H), 3.16 (m, 1H), 2.94 (m, 1H), 2.58 (s, 3H), 1.29 (m, 12H), 1.10 (m, 2H), 0.79 (m, 2H), 0.47 (t, 3H, J=7.3). 13C NMR (75 MHz, DMSO-d6): δ 197.1, 152.3, 151.6, 149.6, 147.2, 144.2, 141.6, 134.0, 129.7, 128.5, 127.2, 126.5, 125.4, 123.0, 73.0, 33.0, 31.1, 26.4, 24.0, 23.9, 23.8, 23.0, 17.9, 12.9. IR (CHCl3, cm−1): 2963, 2934, 2872, 1681. MS [EI+] 404 (M+H)+. Analytical (C27H33NO2): Calculated C, 80.36; H, 8.24; N, 3.47. Found: C, 79.98; H, 8.57; N, 3.46.
