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Into a 250 ml 3-necked roundbottom flask, was placed a solution of 5-chloro-3-nitro-1H- pyrrolo[3,2-b]pyridine (1.1 g, 5.56 mmol, 1.00 equiv) in 1,4-dioxane (30 ml). To this was added HCl (6mol/L) (15 ml, 90 mmol, 16.00 equiv). This was followed by the addition of a solution of Fe (2.5 g, 44.64 mmol, 8.00 equiv) in MeOH (50 ml). The resulting solution was allowed to react, with stirring, for 3 hours while the temperature was maintained at reflux in a bath of oil. A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was diluted with H2O. Adjustment of the pH to 7-8 was accomplished by the addition of Na2CO3. The resulting solution was extracted three times with 100 ml of EtOAc and the organic layers combined and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 1.3 g (crude) of 5-chloro-1H-pyrrolo[3,2-b]pyridin-3-amine as a black solid.
With sulfuric acid; potassium nitrate at 0 - 20℃; for 2h;
1 Step 1: 5-chloro-3-nitro-1H-pyrrolo [3,2-b pyridine
5-Chloro- 1H-pyrrolo[3,2-b]pyridine (3.0 g, 19.7 mmol, 1.0 equiv.) was dissolved in concentrated H2SO4 (5 mL) and cooled to 0 °C, then KNO3 (2.4 g, 23.8 mmol, 1.2 equiv.) was added in portions, maintaining the solution at 0 °C. The reaction mixture was stirred for 2 hours at ambient temperature and then quenched by the addition of water. The resulting solution was adjusted to pH 9 with saturated aqueous NaHCO3. The resulting mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum to 5-chloro-3-nitro- l H-pyrrolo[3,2-b]pyridine (3.1 g) as a yellow solid. LCMS Method BA: [M+H]+ = 198.
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