Methanol → HCID 131726996, compound

Participants

Reaction Steps

Aqueous sodium carbonate (0.18 mL, 2.0 M) is added to a stirred solution of [2-(2-bromo-4-fluoro-phenoxy)-ethyl]-[2-(isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester (0.101 g, 0.179 mmol), 2-fluorophenyl boronic acid (26 mg, 0.19 mmol), Pd(dppb)2Cl2 (43 mg, 0.072 mmol) in DMF (3 mL)/MeOH (0.8 mL). The resultant mixture is heated at 80° C. under argon for 16 hours. At ambient temperature ethyl acetate (10 mL) and brine (3 mL) are added to the mixture, the organic layer is separated, dried, filtered and concentrated. After MPLC separation on silica (gradient 0-1% methanol in methylene chloride), 90 mg (86% yield) of the BOC-protected title compound is obtained. The precursor is dissolved in methylene chloride (10 mL), then a small stream of anhydrous HCl gas is bubbled through the solution for 1 minute. The solution is capped with a glass stopper and allowed to stir for 1 hour to form a suspension. After filtration and drying, 70 mg (86% yield) of the title compound is obtained as a solid. ESIMS: m/z 484 (M+H)+.

Provenance & Evidence