1H-Pyrrolo[2,3-c]pyridine-5-carboxylicacid(9CI)

1H-Pyrrolo[2,3-c]pyridine-5-carboxylicacid(9CI) Property

Boiling point:

471.1±25.0 °C(Predicted)

Density 

1.506±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

1.40±0.30(Predicted)

Appearance

Yellow to brown Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

1H-Pyrrolo[2,3-c]pyridine-5-carboxylicacid(9CI) Chemical Properties,Usage,Production

Synthesis

1H-pyrrolo[2,3-c]pyridine-5-carboxaldehyde (500 mg, 3.42 mmol) was used as starting material, which was dissolved in 1.5 mL of formic acid. The reaction solution was cooled in an ice bath, and 30% aqueous hydrogen peroxide solution (722 μL, 6.8 mmol) was added slowly and dropwise, keeping the reaction system stirred in an ice bath for 1 h. The reaction system was then left to stand at 5 °C overnight. Upon completion of the reaction, the reaction solution was diluted with deionized water, and the resulting solid was collected, washed with deionized water and dried to give 522 mg of an off-white solid. The formate was dissolved in 7 mL of deionized water, 3 mL of 2N sodium hydroxide solution was added, and the pH was adjusted with 5% aqueous hydrochloric acid to 3. The precipitate precipitated was collected and dried to give 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (67% yield). High resolution mass spectrometry (FAB) analysis resulted in a theoretically calculated value of 163.0508 for C8H6N2O2 + H and a measured value of 163.0507 (M + H). In Example 23(i), the target product can be obtained by coupling exo-[2.2.1]-3-amine or endo-[2.2.1]-3-amine with 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid.

References

[1] Tetrahedron, 1990, vol. 46, # 9, p. 3245 - 3266
[2] Synthesis, 1993, # 3, p. 295 - 297
[3] Patent: US2003/153595, 2003, A1
[4] Patent: US2003/45540, 2003, A1
[5] Patent: WO2004/39815, 2004, A2. Location in patent: Page 58