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5-Bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine is a useful intermediate for organic synthesis.

General procedure for the synthesis of 5-bromo-3-iodo-7-azaindole from 5-bromo-7-azaindole: Preparation of 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (Intermediate A) [0442]. 5-Bromo-1H-pyrrolo[2,3-b]pyridine (10 g, 50.76 mmol) was dissolved in 500 mL of acetone with stirring, followed by the addition of N-iodosuccinimide. The reaction mixture was stirred at room temperature for 20 min. Upon completion of the reaction, the product was pulverized, the white solid was collected by filtration and washed with 100 mL of acetone. The resulting solid was dried under vacuum to afford 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (16.34 g, 100% yield) as a light yellow powder.1H NMR (DMSO-d6, 300 MHz) δ 8.51 (d, J = 2.1 Hz, 1H), 8.22 (s, 1H), 8.02 (d, J = 1.2 Hz, 1H), 8.00 (d, J = 5.1 Hz, 2H), 7.44 (dd, J = 8.7 Hz, 0.6 Hz, 2H), 2.35 (s, 3H); MS ESI (m/z): 322/324 [M + H]+, calculated value 322.

[1] Patent: WO2011/149950, 2011, A2. Location in patent: Page/Page column 162
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9569 - 9585
[3] Patent: WO2014/85795, 2014, A1. Location in patent: Paragraph 0400
[4] Patent: US2015/307492, 2015, A1. Location in patent: Paragraph 0120-0125
[5] Patent: WO2016/26078, 2016, A1. Location in patent: Paragraph 076