3-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine Chemical Properties

Melting point:

240°

Density 

1.878±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

11.30±0.40(Predicted)

Appearance

White to off-white Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2933998090

3-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine Usage And Synthesis

Uses

3-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine is a synthetic organic compound that belongs to the class of organic compounds known as pyrrolo[2,3-b]pyridines. It is used as a research compound for its potential applications in the development of new pharmaceuticals.

Synthesis

Step 1: Synthesis of 3-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine. N-bromosuccinimide (1.08 g, 6.1 mmol) was slowly added to a solution of N,N-dimethylformamide (DMF, 25 mL) containing 5-chloro-1H-pyrrolo[2,3-b]pyridine (0.85 g, 5.5 mmol) and the reaction was stirred for 4 h at room temperature. Upon completion of the reaction, the reaction was quenched by the addition of water (100 mL) to the reaction mixture, followed by extraction with ethyl acetate (EtOAc, 3 x 50 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate gradient elution) to afford the title compound 3-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine (1.28 g, quantitative yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 12.3 (br.s, 1H), 8.30 (d, J = X Hz, 1H), 7.93 (d, J = X Hz, 1H), 7.84 (s, 1H).

References

[1] Patent: WO2014/4863, 2014, A2. Location in patent: Paragraph 0230
[2] Patent: WO2018/200425, 2018, A1. Location in patent: Paragraph 00384
[3] Patent: WO2005/95400, 2005, A1. Location in patent: Page/Page column 345; 347
[4] Patent: WO2016/129933, 2016, A2. Location in patent: Page/Page column 45-46
[5] Patent: WO2011/137022, 2011, A1. Location in patent: Page/Page column 31

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