1-Boc-3-bromo-5-azaindole Chemical Properties

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to off-white Solid

1-Boc-3-bromo-5-azaindole Usage And Synthesis

Synthesis

3.5601 g (18.06 mmol) of 3-bromo-1H-pyrrolo[3,2-c]pyridine and 0.4651 g (3.8 mmol, 21 mol%) of dimethylaminopyridine (DMAP) were dissolved in 80 mL of tetrahydrofuran (THF), and the solution was transferred to a 250 mL three-necked round-bottomed flask. The flask was equipped with a magnetic stirrer, thermocouple, nitrogen inlet and outlet and an ice bath cooling device. At 17 °C, 4.7769 g (21.88 mmol, 1.2 eq.) of di-tert-butyl dicarbonate (Boc2O) was slowly added to the reaction system, and the reaction mixture was continuously stirred until 3-bromo-1H-pyrrolo[3,2-c]pyridine was completely disappeared, and the progress of the reaction was monitored by thin-layer chromatography (TLC) (usually overnight with stirring at room temperature). Upon completion of the reaction, the resulting yellow solution was concentrated on a rotary evaporator and subsequently washed with 100 mL of saturated sodium bicarbonate solution and extracted with dichloromethane (3 x 80 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated again on a rotary evaporator to give 6.57 g of orange solid crude product. The crude product was purified by a CombiFlash fast chromatography system using hexane/ethyl acetate as eluent, resulting in 5.25 g (97% yield) of 3-bromo-1H-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester as a white solid.

References

[1] Patent: WO2010/33981, 2010, A2. Location in patent: Page/Page column 28
[2] Patent: WO2011/113798, 2011, A2. Location in patent: Page/Page column 35
[3] Patent: US2013/102587, 2013, A1. Location in patent: Paragraph 0183; 0184
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2430 - 2433

1-Boc-3-bromo-5-azaindole(192189-16-5)Related Product Information

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