7-Methyl-3-[(2'-nitrobiphen-4-yl)methyl]-2-propyl-3H-imidazo[4,5-b]pyridine → 3-(2'-Aminobiphen-4-yl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

Participants

Reaction Steps

To a solution of 0.475 g (1.23 mmol) of 7-methyl-3-[(2'-nitrobiphen-4-yl)methyl]-2-propyl-3H-imidazo[4,5-b]pyridine in 15 mL of absolute ethanol was added 50 mg of 10% palladium on carbon catalyst and the mixture was hydrogenated at 40 psig of hydrogen on a Parr apparatus. Reduction was complete after 1 hour and the reaction mixture was filtered and evaporated in vacuo to afford a tan solid (0.416 g, 95%) which was used in the subsequent step without further purification: NMR (CDCl3) δ 0.98 (t, J=8 Hz, 3H), 1.70-1.86 (m, 3H), 2.66 (s, 3H), 2.83 (t, J=10 Hz, 2H), 3.64-3.72 (br s, 2H), 5.52 (s, 2H), 6.70-6.82 (m, 2H), 7.00-7.19 (m, 5H), 7.36 (d, J=10 Hz, 2H), 8.20 (d, J=6 Hz, 1H); MS (FAB) m/e 357 (MH+).

Provenance & Evidence