Methylamine → 6-Bromo-N-methylpicolinamide

Participants

Reaction Steps

6-Bromopicolinic acid (Aldrich) was coupled with methyl amine using carbonyl diimidazole (CDI) as coupling reagent to afford 6-bromopyridine-2-carboxylic acid methylamide. The 6-bromopyridine-2-carboxylic acid methylamide underwent Suzuki coupling with 4-phenoxyphenylboronic acid, in the presence of tetrakis(triphenylphosphine)palladium as catalyst to give 6-(4-phenoxyphenyl)pyridine-2-carboxylic acid methylamide as a solid. 1H NMR (CDCl3): δ 8.12 (d, J=7.8 Hz, 1H), 7.98 (d, J=8.7 Hz, 2H), 7.90 (t, J=7.8 Hz, 1H), 7.81 (d, J=7.8 Hz, 1H), 7.38 (t, J=8.4 Hz, 2H), 7.18-7.06 (m, 5H), 3.08 (d, J=5.4 Hz, 3H).

Provenance & Evidence