Hydrochloric Acid → 2-(4-Tert-butyl-phenyl)-3-methyl-7-[(pyridin-4-ylmethyl)-amino]-2,3-dihydro-isoindol-1-one

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Reaction Steps

The mixture of 7-amino-2-(4-tert-butyl-phenyl)-3-methyl-2,3-dihydro-isoindol-1-one (0.11 g, 0.37 mmol, Step G), 4-pyridinecarboxaldehyde (0.14 mL, 0.93 mmol), and NaBH(OAc)3 (0.41 g, 1.85 mmol) in 5 mL of 1,2-dichloroethane was stirred at RT for 48 h, and diluted with 20 mL of EtOAc. 1.0 N HCl (aq) was added to bring pH to 1-2. After stirring for 30 min, NaHCO3 (aq) was added to bring pH to 10. The organic portion was washed with brine, condensed, and the titled compound was obtained as a white solid after flash column chromatography (0 to 35% of EtOAc in CH2Cl2). MS (ES+): 386.3 (M+H)+. Calc'd for C25H27N3O-385.50

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