3-Iodo-7-azaindole

Chemical Properties

Solid

Synthesis

4.2.1 Synthesis of 3-iodo-1H-pyrrolo[2,3-b]pyridine (2) 1H-pyrrolo[2,3-b]pyridine (1.00 g, 8.47 mmol) was dissolved in ethanol (40 mL), followed by the sequential addition of iodine (3.23 g, 12.71 mmol), potassium iodide (2.11 g, 12.71 mmol) and 1M sodium hydroxide solution (12.71 mL, 12.71 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the reaction solution was diluted with water and extracted with ethyl acetate (3 times). The organic phases were combined, washed sequentially with 5% sodium thiosulfate solution (twice) and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated to give an orange solid crude product. The crude product was recrystallized from a solvent mixture of methanol and water to give the pure product 3-iodo-1H-pyrrolo[2,3-b]pyridine (2.00 g, 97% yield) as an orange solid. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 12.11 (br, 1H), 8.26 (dd, J = 1.5, 4.8 Hz, 1H), 7.72 (d, J = 2.7 Hz, 1H), 7.69 (dd, J = 1.5, 7.8 Hz, 1H), 7.16 (dd, J = 4.8, 7.8 Hz, 1H ). 13C NMR (75 MHz, DMSO-d6) δ (ppm): 148.5, 144.2, 130.9, 128.5, 122.4, 116.9, 54.8.

References

[1] Angewandte Chemie - International Edition, 2012, vol. 51, # 11, p. 2722 - 2726
[2] Organic and Biomolecular Chemistry, 2011, vol. 9, # 9, p. 3139 - 3141
[3] Organic and Biomolecular Chemistry, 2011, vol. 9, # 14, p. 5129 - 5136
[4] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 701 - 719
[5] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 14, p. 5153 - 5163