6-Azaindole

Chemical Properties

crystals

Uses

6-Azaindole is an indole derivative and useful synthetic intermediate.

Synthesis

General procedure for the synthesis of 6-azaindole using 7-chloro-1H-pyrrolo[2,3-c]pyridine as starting material: a suspension of 7-chloro-1H-pyrrolo[2,3-c]pyridine (650 mg, 4.2 mmol) with 10% Pd/C (50 mg) in ethanol (25 mL) was subjected to a hydrogen atmosphere (balloon pressure) and the reaction was stirred at room temperature. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filter cake was washed with ethyl acetate (10 mL). The filtrates were combined, concentrated under reduced pressure and subsequently purified by fast column chromatography (eluent: dichloromethane/methanol/ammonia, 9:1:0.1, v/v) to afford 1H-pyrrolo[2,3-c]pyridine as a white solid (380 mg, 75% yield).

References

[1] Journal of Organic Chemistry, 2002, vol. 67, # 7, p. 2345 - 2347
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9531 - 9540
[3] Patent: US2007/123535, 2007, A1. Location in patent: Page/Page column 43
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5086 - 5098
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4009 - 4022