(6-Dimethylamino-3-nitro-2-pyridyl)acetonitrile → N,N-dimethyl-1H-pyrrolo[3,2-b]pyridin-5-amine

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Reaction Steps

A mixture of (6-dimethylamino-3-nitro-2-pyridyl)-acetonitrile (Compound 5c,2.06 g, 10.0 mmol), Raney nickel (0.70 g, washed thoroughly with absolute ethanol), and absolute ethanol/acetic acid (4:1, 50 mL) was shaken under ahydrogen atmosphere (3 atm) for 3 hours. The resulting mixture was filteredthrough diatomaceous earth (Celite (trademark)), and the filtrate was evaporated under reduced pressure. The residual oil was dissolved in water(25 mL), the pH was adjusted to 10 with sodium carbonate, and the mixture was extracted with methylene chloride (3×25 mL). These extracts werecombined, dried (MgSO4), and evaporated under reduced pressure to yield an oil. This oil was dissolved in ethyl acetate (10 mL), and this solution was passed through an alumina (basic) filter (approximately 100 g) followed by ethyl acetate (1500 mL). The resulting filtrate was evaporated under reduced pressure to yield Compound 7j (0.44 g, 2.73 mmol,27%) as a white solid: mp, 149.0°-151.0° C.; IR

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