tert-Butyl [5-({5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)pyridin-3-yl]carbamate → tert-Butyl [5-(2-{5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethyl)pyridin-3-yl]carbamate

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Reaction Steps

To a solution of tert-butyl [5-({5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)pyridin-3-yl]carbamate (1.50 g, 3.53 mmol) in methanol (30 mL) was added 10% palladium on carbon (150 mg, 0.141 mmol), and the mixture was hydrogenated under 25 psi of H2 for 2 hours with shaking. The solution was filtered through a pad of celite, and filtrate was concentrated. The residue was purified by flash column chromatography to give the desired product (1.40 g, 92%). LCMS calculated for C23H33N4O4(M+H)+: m/z=429.1.

Provenance & Evidence