Reaction Steps
3-(6,7-Dimethoxy-1-methylisoquinolin-3-yl)phenyl trifluoromethanesulfonate (130 mg), 4-t-butylphenylboronic acid (108 mg, 2 eq.), Pd(OAc)2 (7 mg, 0.1 eq.), XPhos (29 mg, 0.2 eq.), and K2CO3 (147 mg, 3.5 eq.) in 3 mL ACN and 1.5 mL H2O were combined in a flask and degassed. Reaction mixture was heated to 95° C. for 2 hours. Solution was then cooled to room temperature, diluted with EtOAc, and washed with saturated NaHCO3. Organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 40% EtOAc/hexane yielding product as a white solid (121 mg, 97% yield). 1H NMR (400 MHz) (CDCl3) δ 8.35-8.34 (m, 1H), 8.08 (d, J=8 Hz, 1H), 7.88 (s, 1H), 7.68 (d, J=8 Hz, 2H), 7.63 (d, J=8 Hz, 1H), 7.56 (t, J=16 Hz, 1H), 7.53 (d, J=8 Hz, 2H), 7.33 (s, 1H), 7.16 (s, 1H), 4.09 (s, 3H), 4.08 (s, 3H), 3.00 (s, 3H), 1.41 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 155.95, 152.67, 150.26, 149.84, 149.25, 141.47, 140.63, 138.58, 133.47, 129.01, 126.95, 126.71, 125.69, 125.65, 125.53, 122.32, 114.47, 105.72, 103.97, 56.02, 34.55, 31.40, 22.74.
