3-Pyridinecarboxaldehyde → 3-Bromo-N-(pyridin-3-ylmethyl)aniline

Participants

Reaction Conditions

Reaction Steps

A solution of 3-bromoaniline (Aldrich; 1.3 equiv.) in methanol (0.4 M) was treated with 3-pyridinecarboxaldehyde (Aldrich; 1.0 equiv.). The solution was heated to reflux for 2 hours. The reaction was cooled to 0° C. and treated slowly with sodium borohydride (3.4 equiv.). After 1 hour the cooling bath was removed and stirring continued overnight. The reaction was concentrated in vacuo. The residue was partitioned between DCM and water. The aqueous phase was back-extracted once with DCM. The combined organics were washed with water and brine. The organic layer was concentrated to a white solid, which was purified via column chromatography eluting with 90:10 DCM/ethyl acetate to give N-(3-bromophenyl)pyridin-3-ylmethylamine. Anal Calcd for C12H11BrN2: C, 54.77; H, 4.21; N, 10.64. Found: C, 54.67; H, 4.19; N, 10.57. MS found 262.99, 264.99 [M+H]+

Provenance & Evidence