Reaction Steps
A sealed tube containing [4-chloro-2-(diethylamino)-3-phenylquinolin-6-yl](1-methyl-1H-imidazol-5-yl)pyridin-4-ylmethanol•TFA (21 mg, 0.029 mmol, Example 99), Pd(PPh3)4 (5.0 mg, 0.0043 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.010 mL, 0.072 mmol), 2.0 M K2CO3 in water (0.050 mL, 0.10 mmol), and 1,2-dimethoxyethane (1.2 mL) was bubbled with N2 for 3 min. After heating at 90° C. for 17 hours, more Pd(PPh3)4 (5.0 mg, 0.0043 mmol), 2.0 M K2CO3 in water (0.040 mL, 0.080 mmol), and 1,4-dioxane (1 mL) were added. The mixture was heated at 130° C. for 16 hours. NH4Cl (aqueous) was added, the organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic phases were dried (Na2SO4), filtered, concentrated, and purified by reverse phase HPLC (water/acetonitrile/0.1% TFA) to give the title compound. 1H NMR (400 MHz, MeOH-d4) δ 9.06 (s, 1H), 8.79 (d, J=6.57 Hz, 2H), 8.25 (d, J=2.02 Hz, 1H), 8.14 (d, J=9.09 Hz, 1H), 7.94 (d, J=6.57 Hz, 2H), 7.88 (dd, J=2.02, 9.09 Hz, 1H), 7.51-7.64 (m, 3H), 7.40 (d, J=6.57 Hz, 2H), 7.20 (s, 1H), 3.69 (s, 3H), 3.46 (q, J=7.07 Hz, 4H), 2.41 (s, 3H), 1.04 (t, J=7.07 Hz, 6H); MS m/e 478.0 [M+H]+.
