Sodium Chloride → 4-(8-Amino-5,6,7,8-tetrahydro-4-isoquinolinyl)benzonitrile

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In a 100 mL round-bottomed flask, (rac)-4-bromo-5,6,7,8-tetrahydroisoquinolin-8-amine (intermediate A-1[D]) (681 mg, 3 mmol) and 4-cyanophenylboronic acid (540 mg, 3.6 mmol) were dissolved in ethanol (54 mL) to give a light brown solution. Na2CO3 (350 mg, 3.3 mmol), dissolved in water (8.9 mL) was added followed by tetrakis(triphenylphosphine)palladium (0) (104 mg, 90 μmol) after evacuation and replacing 5 times with Argon. The solution was then heated at 85° C. overnight. The reaction was treated with an aq. 10% NaCl solution and extracted with AcOEt (3×). The organic phases were washed again with an aq. 10% NaCl solution, dried over Na2SO4, filtered and evaporated under reduced pressure to give 1.39 g brown foam which was purified by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (5 to 7.5%)) and precipitated from CH2Cl2 with n-pentane to give the title compound (605 mg, 81%) as a light brown foam. MS: 250.1 (M+H+).

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