5-BROMO-1H-PYRROLO[2,3-B]PYRIDINE-3-CARBOXYLIC ACID Chemical Properties

Density 

1.946±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

solid

pka

13.34±0.40(Predicted)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36

Safety Statements 

26-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

5-BROMO-1H-PYRROLO[2,3-B]PYRIDINE-3-CARBOXYLIC ACID Usage And Synthesis

Uses

5-Bromo-1H-pyrrolo[2,3-B]pyridine-3-carboxylic acid is an important raw material in organic synthesis. Its derivative, pyrrolopyridine-2-carboxamide, is a glycogen phosphorylase inhibitor used to prevent or treat diabetes, hypertension, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, atherosclerosis, or tissue ischemia, and can also be used as a cardioprotective agent.

Synthesis

The general procedure for the synthesis of 5-bromo-1H-pyrrolo[2,3-B]pyridine-3-carboxylic acid using 5-bromo-7-azaindole and trichloroacetyl chloride as starting materials was as follows: 5-bromo-7-azaindole (10.00 g, 50.75 mmol) was dissolved in dichloromethane (200 mL), followed by the addition of aluminum chloride (34.00 g, 254.99 mmol). stirred for 10 minutes at room temperature. Next, trichloroacetyl chloride (8.6 mL, 77 mmol) was added slowly and the reaction continued to be stirred at room temperature overnight. After completion of the reaction, the reaction mixture was slowly poured into ice water and filtered to collect the white solid. The filtrate was extracted with ethyl acetate (200 mL x 3). The organic phases were combined and concentrated to give a white solid. The solid was dissolved in water (125 mL), triethylamine (50 mL) was added and stirred at room temperature for 24 hours. At the end of the reaction, the solvent was concentrated to remove the solvent, the pH was adjusted to 5-6 with 1.0 M dilute hydrochloric acid, the product was collected by filtration and dried at 50 °C to give the final 5-bromo-1H-pyrrolo[2,3-B]pyridine-3-carboxylic acid (8.20 g, off-white solid) in 67.0% yield.

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 5, p. 2052 - 2070
[2] Patent: CN106336413, 2017, A. Location in patent: Paragraph 0557; 0558; 0559

5-BROMO-1H-PYRROLO[2,3-B]PYRIDINE-3-CARBOXYLIC ACID(849068-61-7)Related Product Information

• 5-bromothiophene-3-carboxylic acid
• 5-BroMo-4-azaindole-3-carbaldehyde
• 5-BroMo-1H-pyrrole-2-carboxylic acid
• 1,2-BENZISOXAZOLE, 5-BROMO-
• 5-Bromo-1-(2methoxyethyl)-1H-indazole
• METHYL 4,5-DIBROMO-1H-PYRROLE-2-CARBOXYLATE
• METHYL 5-BROMO-1H-PYRROLE-3-CARBOXYLATE
• 5-BROMO-1H-PYRROLO[3,2-B] PYRIDINE
• 5-BroMo-[1,2,4]triazolo[4,3-a]pyrazine
• 5-bromo-1H,2H,3H-pyrrolo[3,2-b]pyridin-2-one
• 5-BroMo[1,2,4]triazolo[1,5-a]pyrazine
• 5-BROMOISOQUINOLIN-1(2H)-ONE
• 5-BROMO-1H-INDOL-3-METHYLAMINE
• 5-BROMO-1H-INDAZOL-3-AMINE
• 1H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 5-broMo-
• 1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 5-bromo-
• 5-Bromo-7-azaindole
• 5-BROMO-1H-PYRROLO[2,3-B]PYRIDINE-3-CARBOXYLIC ACID