Acetic Acid → 3-{5-[(2-Bicyclo[2.2.1]hept-2-ylethylamino)methyl]pyridin-2-yl}benzamide

Participants

Reaction Steps

To a suspension of 3-(5-formylpyridin-2-yl)benzamide (Preparation 12, 108 mg, 0.48 mmol) in DCM (75 mL) was added 2-bicyclo[2.2.1]hept-2-ylethylamine (333 mg, 2.39 mmol), AcOH (80 μL, 1.4 mmol) and sodium triacetoxyborohydride (302 mg, 1.42 mmol). The mixture was stirred at rt for 16 h. EtOAc (100 mL) was added and the organic phase washed with aqueous NaHCO3 (30 mL), brine (30 mL) and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (10% MeOH: DCM to 20% MeOH: DCM) to give the title compound: RT=2.62 min; m/z (ES+)=350.0 [M+H]+.

Provenance & Evidence