4-Bromoaniline → 3H-Imidazo[4,5-b]pyridine-6-carboxamide, N-(4-bromophenyl)-2-[(2,6-dichlorophenyl)amino]-5-methoxy-3-methyl-

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Reaction Steps

2 M trimethyl aluminium solution in hexane (0.35 mL, 0.35 mmol) was added to 4-bromo-aniline (50 mg, 0.31 mmol) in 3.0 mL THF and the mixture stirred at ambient temperature for 1 h. Then methyl 2-(2,6-dichlorophenylamino)-5-methoxy-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxylate (0.10 g, 0.26 mmol) was added and the mixture stirred at 60° C. for 16 h. Then methanol and acetic acid were added, the mixture poured into water. The precipitate was filtered off, washed with water and dried. Then the product was purified by preparative HPLC (RP Symmetry C18, 8 μm; eluent gradient: (water+0.15% formic acid)/acetonitrile=85:15→0:100).

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