Production Method 1

126325-50-6

957760-11-1

Reaction Conditions

1.1 Reagents: Potassium acetate ,  Sodium nitrite Solvents: Acetic acid ,  Water ;  10 °C; overnight, rt → 60 °C

Reference

Preparation of enantiomerically enriched aryloazol-2-yl cyanoethylamino parasiticidal compounds

, World Intellectual Property Organization, , ,

Production Method 2

126325-50-6

957760-11-1

Reaction Conditions

1.1 Reagents: Potassium acetate ,  Sodium nitrite Solvents: Water ;  rt; overnight, 60 °C

Reference

Preparation of new polyazo heterocyclic compounds and their uses as fluorescent chromophores

, France, , ,

Production Method 3

126325-50-6

957760-11-1

Reaction Conditions

1.1 Reagents: Potassium acetate ,  Sodium nitrite Solvents: Acetic acid ,  Water ;  13 °C; 66 h, 13 °C → rt
1.2 Reagents: Sodium nitrite Solvents: Water ;  5 h, rt
1.3 Reagents: Sodium bicarbonate Solvents: Water ;  basified, rt

Reference

Preparation of cyclopropyl fused 1,3-oxazin-2-amine compounds as beta-secretase inhibitors and methods of use

, World Intellectual Property Organization, , ,

7-Bromo-1H-pyrazolo[3,4-c]pyridine Raw materials

• 2-bromo-4-methyl-pyridin-3-amine

7-Bromo-1H-pyrazolo[3,4-c]pyridine Preparation Products

• 7-Bromo-1H-pyrazolo[3,4-c]pyridine (957760-11-1)

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• 5. Aggregated-fluorescent detection of PFAS with a simple chip
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7-Bromo-1H-pyrazolo[3,4-c]pyridine: A Comprehensive Overview

7-Bromo-1H-pyrazolo[3,4-c]pyridine (CAS No. 957760-11-1) is a heterocyclic compound that has garnered significant attention in the fields of organic chemistry and pharmacology. This compound belongs to the class of pyrazolopyridines, which are known for their unique structural features and diverse biological activities. The pyrazolo[3,4-c]pyridine core is a fused bicyclic system comprising a pyrazole ring fused to a pyridine ring, creating a rigid and aromatic structure that is highly amenable to functionalization.

The introduction of the bromo substituent at the 7-position of the pyrazolo[3,4-c]pyridine framework introduces electronic and steric effects that can significantly influence the compound's reactivity and biological properties. Recent studies have highlighted the potential of 7-bromo-1H-pyrazolo[3,4-c]pyridine as a versatile building block in medicinal chemistry. For instance, researchers have explored its role in the development of kinase inhibitors, where the bromine substituent serves as an effective electrophilic center for nucleophilic attacks by protein kinase active sites.

One of the most notable applications of 7-bromo-1H-pyrazolo[3,4-c]pyridine is in the synthesis of small molecule inhibitors targeting various disease-related pathways. A study published in *Nature Communications* demonstrated that derivatives of this compound exhibit potent inhibitory activity against tyrosine kinases, which are key players in cancer progression. The brominated derivative was found to bind selectively to the ATP-binding pocket of these kinases, effectively blocking their catalytic activity.

Moreover, 7-bromo-1H-pyrazolo[3,4-c]pyridine has been utilized in the construction of multitarget-directed ligands (MTDLs) designed to simultaneously modulate multiple therapeutic targets. This approach is particularly promising for treating complex diseases such as neurodegenerative disorders and cardiovascular conditions. By leveraging the electronic versatility of the brominated pyrazolopyridine core, researchers have successfully synthesized MTDLs that exhibit improved pharmacokinetic profiles and reduced off-target effects.

The synthesis of 7-bromo-1H-pyrazolo[3,4-c]pyridine typically involves a multi-step process that combines principles from both classical organic synthesis and modern catalytic methodologies. A common approach involves the condensation of an appropriate bromopyridine derivative with a substituted aldehyde or ketone in the presence of an amide catalyst. Recent advancements in transition metal-catalyzed coupling reactions have further expanded the synthetic routes available for constructing this compound.

From a structural standpoint, 7-bromo-1H-pyrazolo[3,4-c]pyridine exhibits a planar geometry due to the aromaticity of both rings. The bromine atom at position 7 introduces a significant electron-withdrawing effect, which enhances the electrophilicity of adjacent positions on the pyrazole ring. This property makes it an ideal substrate for various nucleophilic substitution reactions, enabling further functionalization and diversification.

In terms of physical properties, 7-bromo-1H-pyrazolo[3,4-c]pyridine is typically isolated as a crystalline solid with high melting point characteristics. Its solubility profile varies depending on substituents introduced during synthesis; however, it generally shows moderate solubility in polar solvents such as dichloromethane and DMF. These properties make it suitable for use in both solution-phase organic reactions and solid-phase synthesis techniques.

Recent computational studies have provided deeper insights into the electronic structure and reactivity patterns of 7-bromo-1H-pyrazolo[3,4-c]pyridine. Density functional theory (DFT) calculations reveal that the brominated derivative exhibits enhanced conjugation across its bicyclic system compared to its non-brominated counterparts. This increased conjugation not only stabilizes reactive intermediates but also enhances its ability to participate in π–π interactions with biomolecular targets.

The biological evaluation of 7-bromo-1H-pyrazolo[3,4-c]pyridine derivatives has been extensively documented in recent years. In addition to its role as a kinase inhibitor precursor, this compound has also shown promise in anti-inflammatory and anti-microbial applications. For example, certain derivatives have demonstrated potent inhibitory activity against cyclooxygenase (COX) enzymes and bacterial biofilms—a finding that underscores its potential utility in developing novel therapeutic agents.

Looking ahead, ongoing research into 7-bromo-1H-pyrazolo[3,c]-pyridine continues to explore its potential applications across various domains. Emerging trends include its use as a scaffold for designing fluorescent probes for bioimaging applications and as a component in advanced materials science projects aimed at developing novel optoelectronic devices.

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