Potassium Phosphate, Tribasic → US10023592, Example 190

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1-one (100 mg, 0.35 mmol), the compound from Step 1 (102 mg, 0.32 mmol), K3PO4 (186 mg, 0.88 mmol) and Pd(dppf)Cl2 (29 mg, 0.04 mmol) in dioxane (5 mL) and H2O (1 mL) was purged 3 times with nitrogen and then stirred at 70° C. for 18 hrs under N2. The mixture was filtered and concentrated. The residue was purified by prep-HPLC to give the title compound (56.02 mg, yield: 40.1%) as a light yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.54 (d, J=8.0 Hz, 1H), 7.89 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.69 (s, 1H), 7.64-7.52 (m, 2H), 7.13 (s, 1H), 7.13-7.08 (m, 1H), 6.78 (dd, J1=8.8 Hz, J2=5.6 Hz, 1H), 4.17 (s, 2H), 3.94-3.86 (m, 1H), 3.79-3.72 (m, 1H), 3.72-3.64 (m, 1H), 3.67 (s, 3H), 3.58-3.49 (m, 1H), 3.07 (s, 3H), 2.32-2.18 (m, 1H), 1.76-1.63 (m, 1H). LCMS (M+H)+=399.1 (M+H)+

Provenance & Evidence