3-bromo-1H-pyrrolo[3,2-b]pyridine Chemical Properties

Melting point:

232-238 °C

Boiling point:

346.3±22.0 °C(Predicted)

Density 

1.770±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

solid

pka

12.99±0.40(Predicted)

color 

Yellow to brown

Safety Information

HS Code 

2933998090

3-bromo-1H-pyrrolo[3,2-b]pyridine Usage And Synthesis

Synthesis

Example 3 Synthesis of 3-bromo-4-azaindole: 0.9707 g (8.21 mmol) of 4-azaindole was dissolved in 50 mL of acetonitrile in a 250 mL three-necked, round-bottomed flask equipped with a magnetic stirrer, a thermocouple, a nitrogen inlet, and an ice bath cooling device. At 170 °C, 5.5187 g (24.7 mmol, 3 eq.) of solid CuBr2 was added to the flask in batches over 10 min. The reaction mixture formed a green suspension and was stirred at room temperature until the TLC assay showed the disappearance of the raw material (about 1-2 hours). The reaction mixture was cooled to 10 °C and quenched by slowly adding 60 mL of a methanol solution of 7N ammonia. The resulting blue solution was concentrated by rotary evaporation at room temperature and the residue was extracted with ethyl acetate (3 x 80 mL). The organic phases were combined, dried with Na2SO4, filtered and concentrated by rotary evaporation to give 1.4 g of an off-white solid. The solid was suspended in 100 mL of hexane, filtered and dried in vacuum to give 1.225 g (76% yield) of 3-bromo-4-azaindole as a white solid.

References

[1] Patent: US2008/9514, 2008, A1. Location in patent: Page/Page column 26
[2] Patent: WO2010/33980, 2010, A2. Location in patent: Page/Page column 28
[3] Synlett, 2007, # 2, p. 211 - 214
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3238 - 3242
[5] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2430 - 2433

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