2-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridine → 4-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-phenylamine

Participants

Reaction Steps

To a solution of 6.81 g (21.0 mmol) of the product of Step A dissolved in 75 mL methanol in a high pressure reaction vessel was added 0.3 g 5% palladium on carbon. The resulting suspension was pressurized to 40 psi with H2 and shaken for 2 hours. The solution was filtered through a pad of celite and the filtrate concentrated to a gray-green oil which crystallized on standing. The crude material was flash chromatographed with 50% ethyl acetate/hexane and 3% methanol/ethyl acetate to yield 5.0 g (85%) of the title compound.

Provenance & Evidence