7-CHLORO-1H-PYRROLO[2,3-C]PYRIDINE Chemical Properties

Melting point:

123-124 °C

Boiling point:

335.8±22.0 °C(Predicted)

Density 

1.425±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

13.08±0.40(Predicted)

Appearance

Off-white to light brown Solid

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41

Safety Statements 

26-36/37/39-39

RIDADR 

2811

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

2933399990

7-CHLORO-1H-PYRROLO[2,3-C]PYRIDINE Usage And Synthesis

Uses

7-Chloro-6-azaindole is a laboratory chemicals, used in food, drug, pesticide or biocidal product.

Synthesis

The general procedure for the synthesis of 7-chloro-1H-pyrrolo[2,3-c]pyridine from 2-chloro-3-nitropyridine and vinylmagnesium bromide was as follows: 2-chloro-3-nitropyridine (10.0 g, 63.07 mmol) was dissolved in 500 mL of anhydrous tetrahydrofuran (THF) and magnetically stirred at -78 °C. An excess of vinylmagnesium bromide (1 M THF solution, 200 mL, 200.0 mmol) was added slowly dropwise, and after completion of the dropwise addition, the reaction mixture was slowly warmed to -20 °C and kept for 16 hours. Subsequently, saturated aqueous ammonium chloride solution (300 g/L, 150 mL, 841.25 mmol) was added dropwise under vigorous stirring to quench the reaction. The resulting suspension was filtered through Hyflo Super Cel filter aid (pre-calcined treatment) and extracted with ethyl acetate (EtOAc, 3×). The organic phases were combined and concentrated, and finally purified by automated fast column chromatography (eluent: dichloromethane/methanol, 97:3, followed by dichloromethane/methanol/ammonium hydroxide, 980:18.75:1.25) to afford the pure product, 7-chloro-1H-pyrrolo[2,3-c]pyridine (3.87 g, 38% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 8.73 (s, 1H), 8.04 (d, J = 5.5 Hz, 1H), 7.53-7.46 (m, 1H), 7.43 (dd, J = 6.2, 3.4 Hz, 1H), 6.64 (dd, J = 3.1, 2.1 Hz, 1H).

References

[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4009 - 4022
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5086 - 5098
[3] Patent: WO2010/51781, 2010, A1. Location in patent: Page/Page column 48
[4] Patent: US2011/263541, 2011, A1. Location in patent: Page/Page column 35
[5] Patent: WO2017/120429, 2017, A1. Location in patent: Page/Page column 258

7-CHLORO-1H-PYRROLO[2,3-C]PYRIDINE(357263-41-3)Related Product Information

• 1H-Pyrrolo[3,2-c]pyridine, 7-chloro-
• 7-chloro-1H-imidazo[4,5-b]pyridine
• 5-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE
• 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid
• 4-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE-3-CARBOXYLIC ACID
• methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate
• 6-chloro-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid
• 3-bromo-4-chloro-1H-pyrrolo[3,2-c]pyridine
• methyl 5-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate
• METHYL 7-CHLORO-1H-PYRROLO[3,2-B]PYRIDINE-2-CARBOXYLATE
• 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
• 3-BROMO-4-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE
• ethyl 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate
• ethyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate
• 6-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE
• 3-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE
• 4-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE,4-Chloro-1H-pyrrolo[2,3-β]pyridine
• METHYL 6-CHLORO-1H-PYRROLO[3,2-B]PYRIDINE-3-CARBOXYLATE