Production Method 1

1036712-62-5

923022-40-6

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ;  2 d, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  cooled

Reference

Preparation of pyrazole-4-carboxamides and imidazole-4-carboxamides as selective plasma kallikrein inhibitors

, World Intellectual Property Organization, , ,

Production Method 2

77771-02-9

22483-09-6

923022-40-6

Reaction Conditions

1.1 Solvents: Toluene ;  overnight, rt
1.2 Reagents: Phosphorus pentoxide ,  Sulfuric acid Solvents: Water ;  1 h, 160 °C; 160 °C → rt
1.3 Reagents: Water ;  cooled
1.4 Reagents: Sodium hydroxide Solvents: Water ;  pH 8, cooled

Reference

Preparation of substituted pyrimidine derivatives as antagonists of the histamine H4 receptor

, World Intellectual Property Organization, , ,

Production Method 3

77771-02-9

22483-09-6

923022-40-6

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ;  2 h, rt
1.2 Reagents: Sodium borohydride Solvents: Ethanol ;  rt; overnight, rt
1.3 Reagents: Tosyl chloride ,  Pyridine Solvents: Dichloromethane ;  0 °C; 0 °C → rt
1.4 Reagents: Aluminum chloride Solvents: Dichloromethane ;  0 °C; 2 h, 50 °C; 50 °C → 0 °C
1.5 Reagents: Water ;  cooled

Reference

Preparation of substituted isoquinolines and isoquinolinones as rho kinase inhibitors for therapy

, World Intellectual Property Organization, , ,

Production Method 4

77771-02-9

22483-09-6

923022-40-6

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ;  2 h, rt
1.2 Reagents: Sodium borohydride Solvents: Ethanol ;  rt; overnight, rt
1.3 Reagents: Acetic acid
1.4 Reagents: Pyridine Solvents: Dichloromethane
1.5 Reagents: Tosyl chloride Solvents: Dichloromethane ;  0 °C; 0 °C → rt; rt
1.6 Reagents: Aluminum chloride Solvents: Dichloromethane ;  0 °C; 2 h, 50 °C; 50 °C → 0 °C
1.7 Reagents: Water ;  cooled

Reference

6-Substituted isoquinolines and isoquinolinones as Rho, PKA and PKG kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases

, World Intellectual Property Organization, , ,

Production Method 5

77771-02-9

22483-09-6

923022-40-6

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ;  2 h; rt
1.2 Reagents: Sodium borohydride Solvents: Ethanol ;  rt; overnight, rt
1.3 Reagents: Acetic acid ;  rt
1.4 Reagents: Tosyl chloride ,  Pyridine Solvents: Dichloromethane ;  0 °C; 0 °C → rt; rt
1.5 Catalysts: Aluminum chloride Solvents: Dichloromethane ;  overnight, rt

Reference

Cycloalkylamine substituted isoquinoline and isoquinolinone derivatives as Rho-kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases

, World Intellectual Property Organization, , ,

Production Method 6

77771-02-9

22483-09-6

923022-40-6

Reaction Conditions

1.1 Solvents: Toluene ;  overnight, rt
1.2 Reagents: Phosphorus pentoxide ,  Sulfuric acid Solvents: Water ;  1 h, 160 °C; cooled
1.3 Reagents: Water ;  cooled
1.4 Reagents: Sodium hydroxide Solvents: Water ;  pH 8, cooled

Reference

Preparation of 4,6-disubstituted 2-amino-pyrimidines as histamine H4 receptor modulators

, World Intellectual Property Organization, , ,

Production Method 7

1036712-62-5

923022-40-6

Reaction Conditions

1.1 Catalysts: Aluminum chloride Solvents: Dichloromethane ;  4 h, rt; overnight, rt

Reference

Cycloalkylamine substituted isoquinolone and isoquinolinone derivatives as Rho kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases

, World Intellectual Property Organization, , ,

Production Method 8

77771-02-9

22483-09-6

923022-40-6

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ;  4 h, reflux; reflux → rt
1.2 Reagents: Sodium borohydride Solvents: Ethanol ;  2 h, rt; overnight, rt
1.3 Reagents: Acetic acid
1.4 Reagents: Tosyl chloride Solvents: Dichloromethane ,  Pyridine ;  3 h, rt
1.5 Reagents: Aluminum chloride Solvents: Dichloromethane ;  4 h, rt; overnight, rt
1.6 Reagents: Water ;  cooled

Reference

Substituted isoquinoline and isoquinolinone derivatives and their preparation and use in the treatment of Rho-kinase associated diseases

, World Intellectual Property Organization, , ,

Production Method 9

77771-02-9

22483-09-6

923022-40-6

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ;  2 h, rt; cooled
1.2 Reagents: Sodium borohydride Solvents: Ethanol ;  rt; overnight, rt
1.3 Reagents: p-Toluenesulfonic acid ,  Pyridine Solvents: Dichloromethane ;  0 °C; 0 °C → rt; rt
1.4 Reagents: Aluminum chloride Solvents: Dichloromethane ;  overnight, rt
1.5 Reagents: Water ;  cooled

Reference

Preparation of piperidinyl isoquinolone derivatives as Rho-kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 10

77771-02-9

22483-09-6

923022-40-6

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ;  2 h
1.2 Reagents: Sodium borohydride Solvents: Ethanol ;  rt; overnight, rt
1.3 Reagents: Acetic acid
1.4 Reagents: Pyridine Solvents: Dichloromethane ;  0 °C
1.5 Reagents: Tosyl chloride Solvents: Dichloromethane ;  0 °C; 0 °C → rt; rt
1.6 Reagents: Aluminum chloride Solvents: Dichloromethane ;  overnight, rt
1.7 Reagents: Water ;  cooled

Reference

Preparation of cyclohexylamine substituted isoquinolones as Rho-kinase inhibitors

, World Intellectual Property Organization, , ,

7-Bromo-6-fluoroisoquinoline Raw materials

• 3-Bromo-4-fluorobenzaldehyde
• 2,2-dimethoxyethan-1-amine
• Benzenesulfonamide, N-[(3-bromo-4-fluorophenyl)methyl]-N-(2,2-dimethoxyethyl)-4-methyl-

7-Bromo-6-fluoroisoquinoline Preparation Products

• 7-Bromo-6-fluoroisoquinoline (923022-40-6)

• 1. Fe(iii)-mediated isomerization of α,α-diarylallylic alcohols to ketones via radical 1,2-aryl migration?
  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
• 2. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
• 3. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126
• 4. Evolution of dealloying induced strain in nanoporous gold crystals?
  Ross Harder,David C. Dunand,Ian McNulty Nanoscale, 2017,9, 5686-5693
• 5. Dissociation of aryl sulfonyl phthalimide radical anions: relevance to the biological activity of arylsulfonyl amides?
  Abdelaziz Houmam,Emad M. Hamed Chem. Commun., 2012,48, 11328-11330

Introduction to 7-Bromo-6-fluoroisoquinoline (CAS No. 923022-40-6)

7-Bromo-6-fluoroisoquinoline, with the chemical identifier CAS No. 923022-40-6, is a significant compound in the realm of pharmaceutical chemistry and medicinal research. This heterocyclic aromatic molecule has garnered considerable attention due to its versatile structural framework, which makes it a valuable scaffold for the development of novel bioactive agents. The presence of both bromine and fluorine substituents introduces unique electronic and steric properties, enhancing its potential as a precursor in synthetic chemistry and drug discovery.

The isoquinoline core is a well-documented motif in natural products and pharmacologically active molecules. Its structural motif is frequently encountered in alkaloids and other bioactive compounds, exhibiting a broad spectrum of biological activities. The introduction of halogen atoms, particularly bromine and fluorine, into the isoquinoline framework has been strategically employed to modulate physicochemical properties such as lipophilicity, metabolic stability, and binding affinity to biological targets. This modification has enabled researchers to fine-tune the pharmacological profile of derivatives, making them more suitable for therapeutic applications.

In recent years, 7-Bromo-6-fluoroisoquinoline has been extensively explored in academic and industrial research settings. Its utility as an intermediate in the synthesis of more complex molecules has been demonstrated in multiple studies. For instance, researchers have leveraged this compound to develop inhibitors targeting various enzymatic pathways implicated in diseases such as cancer, inflammation, and infectious disorders. The bromine atom, in particular, serves as a versatile handle for further functionalization via cross-coupling reactions, including Suzuki-Miyaura and Buchwald-Hartwig couplings, which are pivotal in constructing biaryl systems prevalent in many drugs.

The fluorine substituent at the 6-position contributes to the compound's metabolic stability by resisting degradation pathways that often affect aromatic compounds. This feature is particularly advantageous in drug design, where prolonged half-life can enhance therapeutic efficacy while minimizing side effects. Moreover, fluorine atoms can influence the binding interactions of molecules with biological targets by modulating hydrophobicity and electronic distribution. Such properties have made 7-Bromo-6-fluoroisoquinoline a cornerstone in the development of kinase inhibitors, which play a crucial role in oncology therapy.

Recent advancements in computational chemistry have further illuminated the potential of 7-Bromo-6-fluoroisoquinoline as a drug-like scaffold. Molecular modeling studies have revealed that derivatives of this compound can effectively interact with protein binding pockets through hydrogen bonding networks and hydrophobic interactions. These insights have guided the optimization of lead compounds toward improved pharmacokinetic profiles and target specificity. Additionally, high-throughput screening campaigns have identified novel analogs derived from 7-Bromo-6-fluoroisoquinoline that exhibit promising activity against resistant bacterial strains, highlighting its significance in addressing antimicrobial challenges.

The synthesis of 7-Bromo-6-fluoroisoquinoline itself represents a fascinating challenge for organic chemists. While multiple synthetic routes have been reported, recent methodologies have emphasized greener approaches and improved yields through catalytic processes. For example, transition metal-catalyzed cyclizations have enabled the efficient construction of the isoquinoline core under mild conditions, reducing reliance on harsh reagents or high temperatures. Such innovations align with the growing emphasis on sustainable chemistry practices within the pharmaceutical industry.

The biological evaluation of 7-Bromo-6-fluoroisoquinoline derivatives continues to evolve with emerging technologies such as CRISPR-based screening platforms and artificial intelligence-driven drug design algorithms. These tools have accelerated the identification of potent compounds from complex libraries containing derivatives of this scaffold. Notably, several preclinical studies have demonstrated that certain analogs exhibit selective inhibition of aberrant signaling pathways in cancer cells while sparing healthy tissues. This selectivity is critical for developing next-generation therapeutics with improved safety margins.

Looking ahead, the future prospects for 7-Bromo-6-fluoroisoquinoline appear promising as research efforts continue to uncover new applications for this versatile intermediate. Exploration into its role as a building block for antiviral agents has gained traction amid global health challenges, underscoring its adaptability across diverse therapeutic domains. Furthermore, collaborations between academia and industry are fostering innovation by combining expertise in synthetic chemistry with cutting-edge biophysical techniques to accelerate drug discovery pipelines.

In summary,7-Bromo-6-fluoroisoquinoline (CAS No. 923022-40-6) stands as a pivotal compound in modern medicinal chemistry due to its structural versatility and functional attributes. Its incorporation into drug development programs has yielded several promising candidates entering clinical trials or commercialization phases worldwide. As research methodologies advance—particularly those leveraging computational biology—the potential for harnessing this scaffold will undoubtedly expand further into uncharted therapeutic landscapes.

• 1416372-90-1(6-Bromo-5-fluoroquinoline hydrochloride)
• 679433-94-4(5-bromo-8-fluoro-isoquinoline)
• 127827-51-4(6-bromo-5-fluoro-quinoline)
• 259860-08-7(6-Bromo-5-fluoro-1H-indole)
• 344790-96-1(5-Bromo-4-fluoro-1H-indole)
• 434960-42-6(5-bromo-6-fluoro-1H-Indole)
• 923022-41-7(Isoquinoline, 7-bromo-6-fluoro-, 2-oxide)
• 1420790-22-2(8-bromo-7-fluoro-quinoline)
• 1022091-49-1(6-Bromo-5,7-difluoroquinoline)
• 127827-52-5(6-Bromo-7-fluoroquinoline)