Hydrazine → 1-methyl-1H-pyrrolo[2,3-b]pyridin-6-amine

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Reaction Steps

2-(1-Methyl-1H-pyrrolo[2,3-b]pyridin-6-yl)-isoindole-1,3-dione (220 mg, 0.793 mmol) was dissolved in ethanol (4 mL), then hydrazine (0.5 mL, 15.9 mmol) was added. After 16 h, the mixture was concentrated in vacuo and partitioned between ethyl acetate and water. The aqueous layer was extracted twice more with ethyl acetate, then the combined organic extracts were washed with brine, dried (sodium sulfate), filtered, and concentrated in vacuo. Purification by chromatography (silica, 10 to 50% ethyl acetate in hexanes) gave 1-methyl-1H-pyrrolo[2,3-b]pyridin-6-ylamine (115 mg, 98%) as an off-white solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.67 (d, J=8.3 Hz, 1H) 6.87 (d, J=3.4 Hz, 1H) 6.35 (d, J=8.3 Hz, 1H) 6.30 (d, J=3.4 Hz, 1H) 4.38 (br. s., 2H) 3.76 (s, 3H); LCMS (EI/CI) m/z: 148 [M+H].

Provenance & Evidence