Potassium Carbonate → Ethyl acetate hexane

Participants

Reaction Conditions

Reaction Steps

6,7-Dimethoxy-1-methylisoquinolin-3-yl trifluoromethanesulfonate (300 mg), 3-t-butylphenylboronic acid (183 mg, 1.2 eq.), Pd(OAc)z (19 mg, 0.1 eq.), XPhos (81 mg, 0.2 eq.), and K2CO3 (354 mg, 3 eq.) were combined in a flask with 9 mL dioxane and 3 mL H2O and degassed. Reaction mixture was then refluxed at 100° C. for 2 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 40% EtOAc/hexane yielding product as a clear oil (245 mg, 83% yield). 1H NMR (400 MHz) (CDCl3) δ 8.14 (s, 1H), 7.92-7.89 (m, 1H), 7.81 (s, 1H), 7.45-7.44 (m, 2H), 7.31 (s, 1H), 7.15 (s, H), 4.08 (s, 3H), 4.07 (s, 3H), 3.00 (s, 3H), 1.44 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 155.86, 152.59, 151.39, 149.88, 149.70, 139.95, 133.48, 128.37, 125.13, 124.16, 123.88, 122.16, 114.45, 105.67, 103.92, 56.03, 55.99, 34.88, 31.48, 22.79.

Provenance & Evidence