Production Method 1

1227266-97-8

867034-96-6

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Methanol ,  Water ;  2 h, rt

Reference

Synthesis and evaluation of RNase L-binding 2-aminothiophenes as anticancer agents

Hwang, Jimin; et al, Bioorganic & Medicinal Chemistry, 2022, 58,

Production Method 2

867034-27-3

867034-96-6

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  1 h, -78 °C; 1 h, -30 °C
2.1 Reagents: Potassium hydroxide Solvents: Methanol ,  Water ;  2 h, rt

Reference

Synthesis and evaluation of RNase L-binding 2-aminothiophenes as anticancer agents

Hwang, Jimin; et al, Bioorganic & Medicinal Chemistry, 2022, 58,

Production Method 3

271-29-4

867034-96-6

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  2 h, rt
2.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  1 h, -78 °C; 1 h, -30 °C
3.1 Reagents: Potassium hydroxide Solvents: Methanol ,  Water ;  2 h, rt

Reference

Synthesis and evaluation of RNase L-binding 2-aminothiophenes as anticancer agents

Hwang, Jimin; et al, Bioorganic & Medicinal Chemistry, 2022, 58,

1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde Raw materials

• 1-(Phenylsulfonyl)-6-azaindole-2-carbaldehyde
• 1H-Pyrrolo[2,3-c]pyridine
• 1-(benzenesulfonyl)-1H-pyrrolo[2,3-c]pyridine

1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde Preparation Products

• 1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde (867034-96-6)

• 1. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554
• 2. An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction?
  Sandip Gangadhar Balwe,Yeon Tae Jeong Org. Biomol. Chem., 2018,16, 1287-1296
• 3. An integrated chip for immunofluorescence and its application to analyze lysosomal storage disorders
  Jie Shen,Ying Zhou,Tu Lu,Junya Peng,Zhixiang Lin,Yuhong Pang,Li Yu Lab Chip, 2012,12, 317-324
• 4. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550
• 5. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines Pyrrolopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines

Comprehensive Overview of 1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde (CAS No. 867034-96-6)

1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde (CAS No. 867034-96-6) is a heterocyclic organic compound that has garnered significant attention in pharmaceutical and agrochemical research due to its unique structural properties. This compound belongs to the pyrrolopyridine family, a class of nitrogen-containing heterocycles known for their diverse biological activities. Researchers are increasingly exploring its potential as a building block for drug discovery, particularly in the development of kinase inhibitors and antiviral agents.

The pyrrolopyridine scaffold is a privileged structure in medicinal chemistry, and the introduction of an aldehyde group at the 2-position (2-carbaldehyde) enhances its reactivity for further derivatization. This feature makes 1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde a valuable intermediate in the synthesis of more complex molecules. Recent studies have highlighted its role in the design of small-molecule therapeutics, especially in targeting protein-protein interactions (PPIs) and modulating enzymatic activity.

In the context of current trends, the demand for heterocyclic compounds like 1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde has surged due to their applications in precision medicine and personalized therapies. The compound's ability to serve as a pharmacophore has made it a subject of interest in AI-driven drug discovery platforms, where computational models predict its binding affinity to various biological targets. This aligns with the growing focus on rational drug design and structure-activity relationship (SAR) studies.

From a synthetic chemistry perspective, 1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde can be prepared through multi-step organic reactions, including Vilsmeier-Haack formylation or Pictet-Spengler cyclization. Its stability under standard laboratory conditions and compatibility with common reagents make it a versatile candidate for high-throughput screening (HTS) and combinatorial chemistry. Researchers often inquire about its solubility, melting point, and storage recommendations, which are critical for experimental reproducibility.

The compound's relevance extends to green chemistry initiatives, where its potential as a biodegradable intermediate is being evaluated. With increasing regulatory emphasis on sustainable synthesis, 1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde offers opportunities for eco-friendly modifications, such as catalytic reductions or solvent-free reactions. This aligns with the broader industry shift toward environmentally benign processes.

In analytical chemistry, 1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde is characterized using techniques like nuclear magnetic resonance (NMR), mass spectrometry (MS), and high-performance liquid chromatography (HPLC). Its distinct spectral signatures facilitate quality control in industrial-scale production. Frequently searched questions include its chromatographic retention time and spectral data interpretation, reflecting the need for standardized analytical protocols.

Looking ahead, the exploration of 1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde in covalent inhibitor design and proteolysis-targeting chimera (PROTAC) development represents a cutting-edge application. Its aldehyde group enables selective conjugation with nucleophilic residues in target proteins, a strategy gaining traction in targeted protein degradation therapies. This positions the compound at the forefront of next-generation drug modalities.

For researchers sourcing 1H-Pyrrolo[2,3-c]pyridine-2-carbaldehyde, considerations around supplier reliability, batch-to-batch consistency, and scalability are paramount. The compound's availability in GMP-grade form further underscores its translational potential. As the scientific community continues to unravel its applications, this molecule remains a cornerstone in the toolkit of medicinal chemists and material scientists alike.

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