1-Boc-3-bromo-5-azaindole

1-Boc-3-bromo-5-azaindole Property

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-Boc-3-bromo-5-azaindole Chemical Properties,Usage,Production

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