Ammonium formate → 4-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-phenylamine

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Reaction Steps

2-Ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridine (4.81 g, 15.5 mmol) obtained in Step 1 was dissolved in methanol (155 mL) and palladium/carbon (10%, wet, 1.65 g, 1.55 mmol) and ammonium formate (9.77 g, 155 mmol) were added to the solution, followed by stirring at room temperature for 40 minutes. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. Water was added to the residue and precipitated crystals were collected by filtration and washed with water. Ethyl acetate-hexane (2:3) was added to the obtained crude crystals and the mixture was stirred under reflux for 1 hour. After cooling to room temperature, the precipitated crystals were collected by filtration to obtain Compound P7 (3.53 g, 12.6 mmol, yield 81.2%).

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