5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine

5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine Property

Melting point:

216-220 °C

Density 

1.878±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

11.33±0.40(Predicted)

form 

powder

Appearance

Off-white to pink Solid

Safety

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

5-Bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 5-bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine from 5-bromo-7-azaindole was as follows: 0.50 g (2.54 mmol) of 5-bromo-1H-pyrrolo[2,3-b]pyridine was dissolved in 10 mL of N,N-dimethylformamide, followed by the addition of 0.37 g (2.79 mmol) of N-chloro-butanedi imide and 0.38 g (2.79 mmol) of dibenzoyl peroxide. The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, it was extracted with ethyl acetate and distilled water and the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography to afford 0.50 g (85.0% yield) of the target compound 5-bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine.1H NMR (DMSO-d6) δ: 12.24 (br s, 1H), 8.35 (s, 1H), 8.14 (s, 1H), 8.03 (d, 1H), 7.81 (m, 1H ), 7.77 (s, 1H), 7.64 (t, 1H).

References

[1] Journal of Organic Chemistry, 2018, vol. 83, # 2, p. 930 - 938
[2] Patent: WO2016/129933, 2016, A2. Location in patent: Page/Page column 48