3-Pyridinecarboxaldehyde → HCID 58828515, compound

Participants

Reaction Steps

To a solution of amine 94 (51 mg, 0.075 mmol) in dichloroethane (2 mL) was added pyridine 3-carboxaldehyde (0.017 mL, 180 mmol). After stirring at RT for 15 min NaBH(OAc)3 (48 mg, 0.23 mmol) was added. After stirring overnight, added 1.2 equiv aldehyde and 1.5 equiv NaBH(OAc)3. After stirring for 5 h, the reaction mixture was diluted with NaHCO3/EtOAc and stirred for 10 min. It was then partitioned between EtOAc and NaHCO3. The organic phase was washed once with brine then dried (Na2SO4) and concentrated. The product was purified by automated flash chromatography (70-100% EtOAc/hexane).

Provenance & Evidence