Sodium Chloride → [2-(7-Phenyl-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester

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Reaction Steps

An aqueous Na2CO3 solution (2M, 7.22 mL) is added to a stirred solution of [2-(7-bromo-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester (3.03 g, 7.04 mmol), phenylboronic acid (0.876 g, 7.18 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.407 g, 0.352 mmol) in 1,4-dioxane (36 mL) at ambient temperature under argon. The resultant mixture is heated at 95° C. for 24 hours. At ambient temperature, EtOAc (200 mL)/CH2Cl2 (50 mL) and half-saturated aqueous NaCl solution (200 mL) are added to the mixture. The organic layer is separated, dried over MgSO4, filtered and concentrated. After chromatography on silica gel (gradient 0-3% CH3OH in CH2Cl2), 2.83 g (6.62 mmol, 94% yield) of the title compound is obtained as a white solid. ESIMS: m/z 428 (M+H)+.

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