4-bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine Chemical Properties

Melting point:

230-231°

Boiling point:

367.8±37.0 °C(Predicted)

Density 

1.878±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.15±0.40(Predicted)

Appearance

Off-white to yellow Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2933998090

4-bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine Usage And Synthesis

Uses

4-bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine inhibits HIV replication in vitro and has shown to be active against both wild type and drug resistant strains of HIV. It also has potential for use as a prophylaxis agent.

Biological Activity

4-Bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine is an azaindole with antiviral activity against HIV. It have been shown to be potent inhibitors of the HIV protease enzyme.

Synthesis

Vinylmagnesium bromide (400 mL, 1.0 M solution in THF) was slowly added dropwise to a stirred solution of 5-bromo-2-chloro-3-nitropyridine (20 g, 84.74 mmol) in anhydrous THF (800 mL) at -78 °C. The reaction mixture was slowly warmed to -20 °C and stirred continuously at this temperature for 8 hours. Upon completion of the reaction, the reaction was quenched with 20% NH4Cl solution (600 mL), followed by extraction of the product with ethyl acetate (2 x 500 mL). The organic layers were combined, washed sequentially with water (200 mL) and brine (200 mL), dried over anhydrous sodium sulfate and concentrated. The resulting crude product was ground with ether (2 × 100 mL) to afford 4-bromo-7-chloro-1H-pyrrolo[2,3-C]pyridine as a brown solid (8 g, 40% yield).1H NMR (400 MHz, DMSO-d6) δ 12.48 (br s, 1H), 8.07 (s, 1H), 7.82 (t, J = 3.2 Hz, 1H), 6.61 (s, 1H); LC/MS: m/z 232 [M+H]+.

References

[1] Patent: WO2014/125408, 2014, A2. Location in patent: Page/Page column 36
[2] Journal of Organic Chemistry, 2002, vol. 67, # 7, p. 2345 - 2347
[3] Patent: WO2014/210255, 2014, A1. Location in patent: Page/Page column 282
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5439 - 5445
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6308 - 6327

4-bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine(425380-38-7)Related Product Information

• 1H-Pyrrolo[3,2-c]pyridine, 7-broMo-4-chloro-
• 7-CHLORO-4-METHYL-1H-PYRROLO[2,3-C]PYRIDINE
• 7-CHLORO-5-METHYL-1H-PYRROLO[2,3-C]PYRIDINE
• 1H-Pyrrolo[2,3-c]pyridine, 4,7-dibroMo-
• 1H-Indole-7-carboxylic acid, 4-broMo-, Methyl ester
• 1H-Indole-7-carbonitrile, 4-broMo-
• 4-BROMO-7-METHOXY-6-AZAINDOLE
• 4-HYDROXY-5-AZAINDOLE
• 4-METHOXY-5-AZAINDOLE
• 7-Aza-2-oxindole-6-carboxylic acid Methyl este
• 3-BROMO-4-METHOXY-5-AZAINDOLE
• 4,6-DICHLORO-1H-PYRROLO-[3,2-C]-PYRIDINE
• 3-Iodo-7-Methoxy-4-azaindole
• 6-Hydroxy-5-azaindole
• 1H-Pyrrolo[3,2-c]pyridine, 4-broMo-7-chloro-
• 4-Methoxy-3-nitro-5-azaindole
• 4-Metyoxy-2-Methyl-7-azaindole
• 7-CHLORO-1H-PYRROLO[2,3-C]PYRIDINE