1H-Pyrrolo[3,2-c]pyridin-2(3H)-one

Base Information

• Chemical Name: 1H-Pyrrolo[3,2-c]pyridin-2(3H)-one
• CAS No.: 134682-54-5
• Molecular Formula: C7H6N2O
• Molecular Weight: 134.137
• Hs Code.: 2933990090
• European Community (EC) Number: 897-526-3
• DSSTox Substance ID: DTXSID10576948
• Nikkaji Number: J403.478C
• Wikidata: Q72466139
• Mol file: 134682-54-5.mol

Synonyms:134682-54-5;1H-Pyrrolo[3,2-c]pyridin-2(3H)-one;1,3-Dihydro-2H-pyrrolo[3,2-c]pyridin-2-one;1,3-dihydropyrrolo[3,2-c]pyridin-2-one;1,3-DIHYDRO-PYRROLO[3,2-C]PYRIDIN-2-ONE;5-AZAOXINDOLE;1H,2H,3H-PYRROLO[3,2-C]PYRIDIN-2-ONE;5-AZA-2-OXINDOLE;SCHEMBL658301;AMY2797;DTXSID10576948;YAUVSURSWJMKFT-UHFFFAOYSA-N;MFCD09832902;AKOS006327061;PB17659;AS-42731;CS-0052558;A806824;A1-00373;W-205448;2H-Pyrrolo[3,2-c]pyridin-2-one,1,3-dihydro-(9CI)

Chemical Property of 1H-Pyrrolo[3,2-c]pyridin-2(3H)-one

Chemical Property:

• Boiling Point: 362.5 °C at 760 mmHg
• PKA: 12.58±0.20(Predicted)
• Flash Point: 173 °C
• PSA: 41.99000
• Density: 1.286 g/cm³
• LogP: 0.71420
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 134.048012819
• Heavy Atom Count: 10
• Complexity: 158

Purity/Quality:

99%, ^*data from raw suppliers

1,3-Dihydro-2H-pyrrolo[3,2-c]pyridin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C=CN=C2)NC1=O

Technology Process of 1H-Pyrrolo[3,2-c]pyridin-2(3H)-one

There total 7 articles about 1H-Pyrrolo[3,2-c]pyridin-2(3H)-one 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: 90.0%

3,3,7-tribromo-1,3-dihydro-2H-pyrrolo[3,2-c]pyridin-2-one (134682-57-8) → 5-azaindolin-2-one (134682-54-5)

Guidance literature:

With acetic acid; zinc; at 20 ℃; for 4h;

DOI:10.3987/COM-14-13036

Reference yield: 62.0%

C7H4Br2N2O (134682-56-7) → 5-azaindolin-2-one (134682-54-5)

Guidance literature:

C₇H₄Br₂N₂O; With formic acid; 5%-palladium/activated carbon; In methanol; for 12h; Reflux; Inert atmosphere;

With potassium carbonate; In water; pH=8 - 9; Saturated solution;

DOI:10.1016/j.ejmech.2011.10.009

Reference yield:

5-azaindole (271-34-1) → 5-azaindolin-2-one (134682-54-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / Br₂ / 2-methyl-propan-2-ol; H₂O

2: 69 percent / H₂ / 10percent Pd-C / ethanol / 3 h / 2280 Torr

With hydrogen; bromine; palladium on activated charcoal; In ethanol; water; tert-butyl alcohol;

DOI:10.1021/jo00015a046

upstream raw materials:

3,3,7-tribromo-1,3-dihydro-2H-pyrrolo[3,2-c]pyridin-2-one

5-azaindole

C₇H₄Br₂N₂O

3-picoline-N-oxide

Downstream raw materials:

C₁₅H₈ClN₃O₂

E/Z-3-(3-chloro-2-fluorobenzylidene)-1,3-dihydropyrrolo[3,2-c]pyridin-2-one

methyl 4-((2S,3R,4S,5R)-4-(3-chloro-2-fluorophenyl)-2-neopentyl-2'-oxo-1',2'-dihydrospiro[pyrrolidine-3,3'-pyrrolo[3,2-c]pyridine]-5-ylcarboxamido)-3-methoxybenzoate

methyl 4-((2R,3S,4R,5S)-4-(3-chloro-2-fluorophenyl)-2-neopentyl-2'-oxo-1',2'-dihydrospiro[pyrrolidine-3,3'-pyrrolo[3,2-c]pyridine]-5-ylcarboxamido)-3-methoxybenzoate

Refernces

Discovery of potent and orally active p53-MDM2 inhibitors RO5353 and RO2468 for potential clinical development

10.1021/ml400359z

The research aims to develop small-molecule MDM2 inhibitors to restore dysfunctional p53 activities for cancer treatment. The study builds on previous work on a non-imidazoline MDM2 inhibitor, RG7388, and explores additional derivatives to expand chemodiversity and identify potent and selective MDM2 antagonists with desirable pharmacological properties. The researchers focused on bioisosteric replacements of the 6-chlorooxindole group in RO8994, leading to the identification of two highly potent, selective, and orally active p53-MDM2 inhibitors, RO2468 and RO5353. These compounds demonstrated excellent in vitro and in vivo pharmacokinetic profiles and significant tumor regression in mouse models at doses comparable to RO8994. The key chemicals used in the research include RO8994, RO2468 (14), and RO5353 (16), along with various analogues such as 4-azaoxindole (I), 5-azaoxindole (II), 7-azaoxindole (III), 2-chloropyrrolo[2,3-d]pyrimidin-6-one (IV), and 2-chlorothienyl[3,2-b]pyrrol-5-one (V). The study concludes that RO2468 and RO5353 have promising potential for clinical development.

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