6-Bromo-1H-pyrrolo[2,3-b]pyridine

Chemical Properties

6-Bromo-1H-pyrrolo[2,3-B]pyridine has high chemical transformation properties, and it has been reported in the literature that the bromine atoms in the structure of the substance can be cross-coupled with metal-organic reagents or metal-organic reagents under the action of metal-palladium catalysts. It is worth noting that the substance is sensitive to oxidants, and its pyrrole and pyridine units are easily oxidized to the corresponding nitrogen oxides when exposed to oxidants.

Uses

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.

Synthesis

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).

References

[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