Potassium Carbonate → 1-[4-methoxy-7-[3-(trifluoromethyl)-1,2,4-triazol-1-yl]-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-[5-(2-pyridyl)-3,4-dihydro-1H-isoquinolin-2-yl]ethane-1,2-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(5-(pyridin-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)ethane-1,2-dione (100 mg, 0.204 mmol), 3-(trifluoromethyl)-1H-1,2,4-triazole (55.8 mg, 0.407 mmol), (1R,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (5.79 mg, 0.041 mmol), copper (I) iodide (19.38 mg, 0.102 mmol) and potassium carbonate (84 mg, 0.611 mmol) in dioxane (1 mL) was heated at 100° C. for 4 hours. LCMS indicated that the desired product was generated. The reaction mixture was filtered and the clear solution was purified by prep. HPLC to give 1-(4-methoxy-7-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(5-(pyridin-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)ethane-1,2-dione as white solid (35 mg, 30%). LCMS: m/e 548.18 (M+H)+, 2.50 min (method 10). 1H NMR (500 MHz, MeOD) δ ppm 2.85-3.08 (m, 2H) 3.74-4.04 (m, 5H) 4.81-5.09 (m, 2H) 7.37-7.71 (m, 3H) 7.88-7.96 (m, 1H) 7.97-8.18 (m, 2H) 8.33-8.43 (m, 1H) 8.52-8.70 (m, 1H) 8.82-8.96 (m, 1H) 9.51 (s, 1H).

Provenance & Evidence