Acetic Acid → Isoquinoline, 1,2,3,4-tetrahydro-5-[2-(1H-imidazol-1-yl)-4-(trifluoromethyl)phenyl]-

Participants

Reaction Steps

A solution of Cl2Pd(AmPhos) (Sigma-Aldrich, St. Louis, Mo., 0.049 g, 0.069 mmol), isoquinolin-5-ylboronic acid (Frontier Scientific, Logan, Utah, 0.297 g, 1.718 mmol), 1-(2-bromo-5-(trifluoromethyl)phenyl)-1H-imidazole (0.400 g, 1.374 mmol), and potassium phosphate (1.167 g, 5.50 mmol) in 6 mL dioxane 3 mL water was heated to 120° C. overnight. The reaction mixture was diluted with diethyl ether. The organics were separated and concentrated. The resulting residue was taken up in 6 mL MeOH, was treated with platinum(IV) oxide (0.031 g, 0.137 mmol) and acetic acid (0.236 ml, 4.12 mmol) and was placed under 45 psi (4559.6 kpa) H2 for 2 hours. The reaction mixture was filtered through a plug of diatomaceous earth eluting with EtOAc. The filtrate was washed with saturated NaHCO3 solution, the organics dried over MgSO4 and concentrated yielding 5-(2-(1H-imidazol-1-yl)-4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.450 g, 1.311 mmol). [M+H]+=344.0

Provenance & Evidence