Reaction Steps
6,7-Dimethoxy-1-methylisoquinolin-3-yl trifluoromethanesulfonate (200 mg), 3-hydroxyphenylboronic acid (157 mg, 2 eq.), Pd(OAc)2 (13 mg, 0.1 eq.), XPhos (54 mg, 0.2 eq.), and Cs2CO3 (650 mg, 3.5 eq.) were combined in a flask with 9 mL ACN and 3 mL H2O and degassed. Reaction mixture was then refluxed at 100° C. for 5 hours. Solution was cooled to room temperature then diluted with EtOAc and washed with saturated NaHCO3. Organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 50% EtOAc/hexane yielding product as white solid (78 mg, 46% yield). 1H NMR (400 MHz) (CDCl3) δ 7.66-7.63 (m, 2H), 7.38 (d, J=4 Hz, 1H), 7.20 (t, J=8 Hz, 1H), 7.17 (s, 1H), 7.00 (s, 1H), 6.73-6.71 (m, 1H), 3.95 (s, 3H), 3.94 (s, 3H), 2.87 (s, 3H). 13C NMR (100 MHz) (CDCl3) δ 156.74, 156.12, 152.88, 149.93, 149.19, 141.46, 133.56, 129.85, 122.35, 118.72, 115.49, 115.25, 114.59, 105.66, 103.87, 56.05, 56.01, 22.20. IR (thin film NaCl) 3002, 2255, 1621, 1576, 1501, 1468, 1425, 1409, 1372, 1324, 1292, 1245, 1222, 1205, 1178, 1159, 1062, 1027, 995, 973, 924, 913, 896, 878, 846, 837, 781, 762, 745, 738, 726, 691, 645.
