Sodium Hydroxide → 6-Bromo-3-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-3H-imidazo[4,5-b]pyridine

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Reaction Steps

A mixture of N-{5-bromo-2-[(cyclopropylmethyl)amino]pyridin-3-yl}-3,3-dimethylbutanamide (5.04 g, 14.8 mmol, step E) and 2 N sodium hydroxide solution (10 mL) in ethanol (90 mL) was stirred under reflux for 21 h. After concentration, the residue was dissolved in water (50 mL) and the mixture was extracted with ethyl acetate (30 mL×2). The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 as eluent) to give the title compound (3.9 g, 82%) as a pale pink solid.

Provenance & Evidence