5-Bromo-7-azaindole Chemical Properties

Melting point:

176-180 °C

Boiling point:

357.4±42.0 °C(Predicted)

Density 

1.79±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

6.25±0.20(Predicted)

form 

Crystalline Powder

color 

White to yellow

InChI

InChI=1S/C7H5BrN2/c8-6-3-5-1-2-9-7(5)10-4-6/h1-4H,(H,9,10)

InChIKey

LPTVWZSQAIDCEB-UHFFFAOYSA-N

SMILES

C12NC=CC1=CC(Br)=CN=2

LogP

1.8 at 25℃ and pH7

CAS DataBase Reference

183208-35-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ALFA

5-Bromo-7-azaindole Usage And Synthesis

Description

5-Bromo-7-azaindole has important applications in drug synthesis and is often used as an intermediate in the synthesis of a variety of bioactive molecules, especially in the development of anti-tumor, anti-viral and neurological drugs. In addition, it can also be used in the research of fluorescent probes to help observe cellular processes in real time.

Chemical Properties

White to light brown powder or crystal

Uses

5-Bromo-7-azaindole is a chemical reagent used in organic syntheses. Used in the synthesis of Venetoclax (A112430), a potent and selective BCL-2 inhibitor that achieves potent antitumour activity while sparing platelets. Also used in other 7-azaindole derivatives such as for PDK1 inihibtors.

Biological Functions

5-Bromo-7-azaindole displays significant cytotoxicity against human ovarian carcinoma cells in vivo and inhibits the proliferation of cancer cells by binding to ATP synthase. The anticancer activity of this compound is due to its ability to inhibit the synthesis of DNA and RNA, which are vital for cell division.

Toxicology

5-Bromo-7-azaindole has acute oral toxicity and specific target organ toxicity.

Synthesis

In the 250 ml flask is sequentially added in 50 ml ethanol and 5-bromo-1-hydrogen pyrrolo [2,3 - the b] pyridine -2 - ketone (4.2g, 20 mmol), Sn powder (4.7 g, 40 mmol) and 5 mol/L hydrochloric acid (14 ml), 40 ℃ stirring for 2 hours, the reaction is completed, to remove the ethanol, add 50 ml of water residue is completely dissolved, saturated NaHCO3 solution and to pH=8, and filtering the resulting solid, after drying, dissolved in 50 ml chloroform, adding CuBr2(13.4 g, 60mmol), 60 Cstirring for 2 hours, the reaction is completed, the end of the reaction, rotary evaporated to remove chloroform, adding 50 ml saturated NaHCO3 solution, ethyl acetate (3 × 100 ml), the combined organic phase with water (50 ml) for washing and then the saturated salt water (50 ml) washing, anhydrous Na2SO4 drying, filtering, the filtrate is concentrated to obtain 5-bromo-1H-pyrrolo [2,3 - the b] pyridine the crude product, the crude product is chloroform: hexane=2:1 (volume ratio) mixed solution recrystallize to get 3.1 g of pale yellow 5-Bromo-7-azaindole pure product, yield 77.6%, melting point:176.8-177.3 ℃.

Solubility in organics

The solubility of 5-Bromo-7-azaindole in pure solvents increases with increasing temperature. Among them 5-Bromo-7-azaindole showed the best solubility in methyl acetate and the worst solubility in hexane. The maximum change in solubility of 5-Bromo-7-azaindole in DCM was observed at T = 298.15-313.15 K. The solubility of 5-Bromo-7-azaindole in DCM was found to be the most variable.

References

[1] Patent: WO2004/78757, 2004, A2. Location in patent: Page 65; 66-67
[2] Patent: CN105461718, 2016, A. Location in patent: Paragraph 0016
[3] Patent: CN107987076, 2018, A. Location in patent: Paragraph 0042; 0054-0057; 0070-0073; 0086-0089
[4] Patent: CN106188050, 2016, A. Location in patent: Paragraph 0021
[5] Patent: EP2070928, 2009, A1. Location in patent: Page/Page column 101

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