4-Pyridinecarboxaldehyde → HCID 11474626, compound

Participants

Reaction Steps

In a 25 mL round bottomed flask, 4-amino-2-(4-tert-butyl-phenyl)-isoindole-1,3-dione (30 mg, 0.101 mmol, Step B) was dissolved in 1,2-dichloroethane (10 mL). To this was added 4-pyridinecarboxaldehyde (0.05 mL, 0.524 mmol). The reaction was stirred for 1 h under N2. NaBH(OAc)3 (40 mg, 0.188 mmol) was added and the suspension was stirred for 6 h. The reaction was quenched with saturated NaHCO3 solution (50 mL). The reaction was rotary evaporated to remove the 1,2-dichloroethane. The product was extracted with EtOAc (3×50 mL). The combined organics were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated to afford an oil. The oil was purified by flash chromatography on silica gel eluting with 30% EtOAc in hexanes. MS (ES+): 386.1 (M+H)+. Calc'd for C24H23N3O2-385.46.

Provenance & Evidence