4-Bromo-7-azaindole Chemical Properties

Melting point:

178-183 °C

Density 

1.770±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

12.95±0.40(Predicted)

form 

Solid

color 

Yellow to orange

InChI

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

InChIKey

LEZHTYOQWQEBLH-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

2933998090

4-Bromo-7-azaindole Usage And Synthesis

Uses

4-Bromo-7-azaindole is an important organic intermediate (building block) to synthetize substituted azaindole products.

Description

4-Bromo-7-azaindole is a small molecule pyridine compound containing a bromine functional group. This substance can be used as a basic structure for the synthesis of other complex organisms. It is also a good reagent and can react with amides, amines, amino acid esters and phenolic compounds through the formation of C-N and C-O bonds.

Chemical Properties

Pale yellow powder

Uses

4-Bromo-7-azaindole is chemical reagent used in the synthesis of tyrosine kinase inhibitors.

Synthesis

1H-pyrrolo[2,3-b]pyridine-7-oxide (3.0 g, 22.4 mmol) was used as starting material, which was co-dissolved with tetramethyl ammonium (4.13 g, 1.2 eq.) in N,N-dimethylformamide (DMF, 30 ml). Dimethyl sulfoxide (Ms2O, 7.8 g, 2.0 eq.) was added in batches at 0 °C. The reaction mixture was stirred at 0 °C for 1 h, then brought to room temperature and continued stirring for 4 h. The reaction was carried out at 0 °C. Upon completion of the reaction, the reaction solution was diluted with water (60 ml) and the pH was adjusted with solid sodium hydroxide (NaOH) to 7. Subsequently, more than 130 ml of water was added and the resultant suspension was kept at 5 °C for 1 h. The reaction was carried out by filtration. The precipitate was collected by filtration, washed with ice water (2 x 20 ml) and dried in a vacuum oven using phosphorus pentoxide (P2O5) as a desiccant to give finally 4-bromo-1H-pyrrolo[2,3-b]pyridine (2.47 g, 56% yield). Mass spectrum (ESI) m/z 196.9 [M + H]+. 1H NMR (400 MHz, CDCl3) δ 10.77 (br s, 1H), 8.14 (d, J = 5.2 Hz, 1H), 7.42 (s, 1H), 7.31 (d, J = 5.1 Hz, 1H), 6.57 (s, 1H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1208 - 1212
[2] Patent: CN101921268, 2016, B. Location in patent: Paragraph 0257; 0265-0268
[3] Patent: WO2010/30727, 2010, A1. Location in patent: Page/Page column 120
[4] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025
[5] Patent: WO2009/140320, 2009, A1. Location in patent: Page/Page column 86

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