Triethylaluminum → 4-[4-(5-Ethyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester

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Reaction Steps

To a stirred solution of 4-[4-(5-Bromo-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester (200 mg, 0.4 mmol) in anhydrous THF (4 mL) under N2 was added dichlorobis(tri-o-tolylphosphine)palladium(II) (14 mg, 0.02 mmol), CeCl3 (99 mg, 0.4 mmol) and AlEt3 (1M in hexanes, 1.5 mL, 1.2 mmol) and the reaction stirred at RT for 4 h. The reaction was quenched with ice, diluted with 0.5M aqueous Rochelle's salts (30 mL) and extracted with EtOAc (3×40 mL). The combined organics were washed with Rochelle's salts (2×50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo and the crude residue purified by reverse phase preparative HPLC-MS to afford 4-[4-(5-ethyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester as an orange solid (83 mg, 61%).

Provenance & Evidence