1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid

Base Information

• Chemical Name: 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid
• CAS No.: 156270-06-3
• Molecular Formula: C8H6N2O2
• Molecular Weight: 162.148
• Hs Code.: 29339980
• European Community (EC) Number: 626-855-5
• DSSTox Substance ID: DTXSID20436221
• Nikkaji Number: J1.378.118D
• Wikidata: Q72505615
• Mol file: 156270-06-3.mol

Synonyms:1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid;156270-06-3;7-AZAINDOLE-3-CARBOXYLIC ACID;1H-Pyrrolo[2,3-b]pyridine-3-carboxylicacid;MFCD07778360;SCHEMBL985214;DTXSID20436221;KYBIRFFGAIFLPM-UHFFFAOYSA-N;7-Azaindole-3-carboxylic acid, 95%;AKOS005071982;CC-0806;CS-W019745;PB23519;NCGC00326021-01;AC-24706;SY013957;AM20050838;FT-0653155;EN300-51102;AB01321260-02;A809728;W-205799;Z385370186

Chemical Property of 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 205-209 °C
• Refractive Index: 1.743
• Boiling Point: 446.822 °C at 760 mmHg
• PKA: 0.52±0.20(Predicted)
• Flash Point: 224.03 °C
• PSA: 65.98000
• Density: 1.507 g/cm³
• LogP: 1.26110
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Slightly soluble in water.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 162.042927438
• Heavy Atom Count: 12
• Complexity: 196

Purity/Quality:

98%, ^*data from raw suppliers

1H-Pyrrolo[2,3-b]pyridine-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(NC=C2C(=O)O)N=C1
• Uses: 7-Azaindole-3-carboxylic acid is a reactant for synthesis of azaindol derivatives as new acrosin inhibitors and for preparation of triazoles via regioselective heterocyclizaiton reactions. It is also a reactant for synthesis of azaindolylcarboxy-endo-tropanamide.

Technology Process of 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid

There total 10 articles about 1H-Pyrrolo[2,3-b]pyridine-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,2,2-trichloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone (163220-69-7) → 7-azaindolyl-3-carboxylic acid (156270-06-3)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 6h;

DOI:10.1016/j.ejmech.2019.07.036

Reference yield: 94.3%

(1H-pyrrolo[2,3-b]pyridin-3-yl)methanol (1065100-83-5) → 7-azaindolyl-3-carboxylic acid (156270-06-3)

Guidance literature:

With potassium permanganate; In dichloromethane; at 50 ℃; for 3h; Temperature;

Reference yield: 6.0%

1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde (4649-09-6) → 7-azaindolyl-3-carboxylic acid (156270-06-3)

Guidance literature:

1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde; With 1-hydroxy-pyrrolidine-2,5-dione; o-iodoxybenzoic acid; In dimethyl sulfoxide; at 20 ℃; for 16h;

With hydrogenchloride; water; sodium chloride; In dimethyl sulfoxide; pH=3 - 4;

upstream raw materials:

7-Azaindole

acetic anhydride

2,2,2-trichloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone

1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde

Downstream raw materials:

1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester

C₁₇H₁₄N₂O₃

C₁₇H₁₃FN₂O₃

C₁₇H₁₃FN₂O₃

Refernces

• 1、 Moir, Michael,Lane, Samuel,Lai, Felcia,Connor, Mark,Hibbs, David E.,Kassiou, Michael. "Strategies to develop selective CB2 receptor agonists from indole carboxamide synthetic cannabinoids". . p. 291 - 309. Retrieved 2019/07/17.
• 2、 Jiang, Jun Hang,Liu, Xue Fei,Zhen, Can Hui,Zhou, You Jun,Zhu, Ju,Lv, Jia Guo,Sheng, Chun Quan. "Acrosin structure-based design, synthesis and biological activities of 7-azaindol derivatives as new acrosin inhibitors". . p. 272 - 275. Retrieved 2012/01/14.