6-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE

Uses

6-Chloro-1H-pyrrolo[2,3-b]pyridine is used in the preparation of heterocyclic compounds for the use of treatment of cancer.

Synthesis

Example 96 Step C: Synthesis of 6-chloro-1H-pyrrolo[2,3-B]pyridine. Ethyl 6-chloro-pyrrolo[2,3-B]pyridine-1-carboxylate (400 mg, 1.78 mmol) was dissolved in methanol (35 mL), followed by the addition of 1N sodium hydroxide solution (13 mL). The reaction mixture was stirred at room temperature for 6 hours. Upon completion of the reaction, the solvent was removed by rotary evaporator. The residue was neutralized with saturated sodium bicarbonate solution and the precipitate was collected by filtration. The precipitate was washed with water and dried by vacuum pump to afford the target product 6-chloro-1H-pyrrolo[2,3-B]pyridine (260 mg, 1.71 mmol, 96% yield). MS (electrospray positive ion mode): m/e = 153.1 ([M+H]+); LC retention time: 2.85 min.

References

[1] Patent: WO2005/28475, 2005, A2. Location in patent: Page/Page column 175
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 23, p. 7107 - 7112
[3] Patent: WO2013/10880, 2013, A1. Location in patent: Page/Page column 103-104
[4] Patent: EP2548876, 2013, A1. Location in patent: Paragraph 0438-0441
[5] Patent: WO2016/112088, 2016, A1. Location in patent: Paragraph 0447