143468-13-7

6-Bromo-1H-pyrrolo[2,3-B]pyridine has high chemical conversion performance. Relevant literature reports that the bromine atom in the structure of this substance can undergo cross-coupling reaction with metal organic reagents or metal-like organic reagents under the action of metal palladium catalyst.

Step 2: To a solution of 1-benzoyl-6-bromo-1H-pyrrolo[2,3-b]pyridine (0.046 g, 0.15 mmol) in methanol (5.0 mL) was added 5 N aqueous sodium hydroxide solution (1.0 mL). The reaction mixture was stirred at room temperature for 2 hours. After the reaction was completed, the solvent was removed by concentration under reduced pressure. The residue was extracted with ether (3 × 10 mL) and the organic layers were combined and washed sequentially with water (10 mL) and saturated sodium chloride solution (10 mL). The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 6-bromo-1H-pyrrolo[2,3-b]pyridine (0.028 g, 95% yield). The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 7.01 (d, J = 8.1 Hz, 1H), 7.46 (d, J = 8.1 Hz, 1H), 7.75 (d, J = 8.1 Hz, 1H), 8.51 (d, J = 8.1 Hz, 1H).

[1] Synthesis, 1992, # 7, p. 661 - 663
[2] Patent: EP2565192, 2013, A1. Location in patent: Paragraph 0283
[3] Patent: WO2011/128455, 2011, A1. Location in patent: Page/Page column 83
[4] Patent: US2011/280808, 2011, A1. Location in patent: Page/Page column 39
[5] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 6, p. 1405 - 1411