Potassium Carbonate → HCID 89815328, compound

Participants

Reaction Steps

A solution of Pd(PPh3)4 (Strem Chemicals Inc., Newburyport, Mass., 0.643 g, 0.557 mmol), 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (1.353 g, 5.57 mmol), tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (ASW Medchem, Brunswick, N.J., 2.000 g, 5.57 mmol), and potassium carbonate (3.08 g, 22.27 mmol) in 12 mL dioxane and 6 mL water was heated to 120° C. for 3 days. The reaction mixture was diluted with diethyl ether, washed with water, the organics dried over MgSO4 and concentrated to provide tert-butyl 5-(2-fluoro-4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate. The resulting residue was dissolved in 10 mL THF and was treated with HCl 4 N in dioxane (9.74 ml, 39.0 mmol), and allowed to stir at room temperature overnight. The reaction mixture was diluted with diethyl ether/heptane, and the resulting solid was filtered and dried yielding 5-(2-fluoro-4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.930 g, 5.82 mmol). [M+H]+=296.1

Provenance & Evidence