Production Method 1

503000-87-1

95652-77-0

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol ;  17 h, 60 °C

Reference

Preparation of bicyclic heterocyclyl compound as SOS1 inhibitor

, World Intellectual Property Organization, , ,

Production Method 2

503000-87-1

95652-77-0

Reaction Conditions

1.1 Reagents: Thionyl chloride ;  3 h, reflux
1.2 Solvents: Methanol ;  3 h, reflux

Reference

Structure-Guided Optimization of HIV Integrase Strand Transfer Inhibitors

Zhao, Xue Zhi; Smith, Steven J.; Maskell, Daniel P.; Metifiot, Mathieu; Pye, Valerie E.; et al, Journal of Medicinal Chemistry, 2017, 60(17), 7315-7332

Production Method 3

38025-90-0

95652-77-0

Reaction Conditions

1.1 Reagents: Silver carbonate Solvents: Chloroform ;  3 h, 50 °C

Reference

Preparation of benzimidazole compounds as peptidylarginine deiminase 4 inhibitors

, World Intellectual Property Organization, , ,

Production Method 4

503000-87-1

95652-77-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  0 °C; 1 h, rt; 2 h, reflux
1.2 Reagents: Sodium carbonate Solvents: Water ;  pH 10

Reference

Preparation of O-lactam substituted phenyl ethers as hemoglobin modulators

, United States, , ,

Production Method 5

503000-87-1

95652-77-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  2 h, rt

Reference

Preparation of thioaryl derivatives as GPR120 agonists

, World Intellectual Property Organization, , ,

Production Method 6

503000-87-1

95652-77-0

Reaction Conditions

1.1 Reagents: Trimethylsilyldiazomethane Solvents: Methanol ,  Dichloromethane ;  0 °C; 10 min, 0 °C

Reference

Pyrazole, triazole and tetrazole orexin receptor antagonists

, World Intellectual Property Organization, , ,

Production Method 7

503000-87-1

95652-77-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  0 °C; 0 °C → rt; 2 h, rt

Reference

First synthesis of methyl 2-amino-6-methoxynicotinate using a combination of microwave and flow reaction technologies

Jeges, Gyorgy; Meszaros, Tamas; Szommer, Tamas; Kovacs, Jozsef; Nagy, Tamas; et al, Synlett, 2011, (2), 203-206

Production Method 8

1073230-28-0

95652-77-0

Reaction Conditions

1.1 Solvents: Methanol ;  1 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  basified

Reference

Preparation of naphthyridinone analogs as mGluR5 positive allosteric modulators

, World Intellectual Property Organization, , ,

Production Method 9

503000-87-1

95652-77-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Thionyl chloride ;  5 h, reflux; reflux → rt
1.2 Solvents: Methanol ;  1 h, reflux; reflux → rt

Reference

Synthesis and Structure-Affinity Relationships of Novel N-(1-Ethyl-4-methylhexahydro-1,4-diazepin-6-yl)pyridine-3-carboxamides with Potent Serotonin 5-HT3 and Dopamine D2 Receptor Antagonistic Activity

Hirokawa, Yoshimi; Fujiwara, Iwao; Suzuki, Kenji; Harada, Hiroshi; Yoshikawa, Takashi; et al, Journal of Medicinal Chemistry, 2003, 46(5), 702-715

Production Method 10

503000-87-1

95652-77-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Catalysts: Dimethylformamide Solvents: Dichloromethane ;  2.5 h, 40 °C
1.2 Solvents: Methanol ;  0 °C; 1 h, rt

Reference

Preparation of arylcarboxamides for the treatment of diseases and use in cosmetics

, World Intellectual Property Organization, , ,

Production Method 11

18107-18-1

503000-87-1

95652-77-0

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Methanol ,  Dichloromethane ;  20 min, 0 °C; 0 °C → rt; 20 min, rt

Reference

From 2,6-dichloronicotinic acid to thiopeptide cores

Just-Baringo, Xavier; Albericio, Fernando; Alvarez, Mercedes, European Journal of Organic Chemistry, 2013, 2013(28), 6404-6419

Production Method 12

503000-87-1

95652-77-0

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  0 °C; 0 °C → 80 °C; 16 h, 80 °C; 80 °C → 27 °C
1.2 Reagents: Water ;  cooled

Reference

Indazolylquinazolinone derivatives as inhibitors of human immunodeficiency virus replication and their preparation

, World Intellectual Property Organization, , ,

Production Method 13

38025-90-0

95652-77-0

Reaction Conditions

1.1 Reagents: Silver carbonate Solvents: Chloroform ;  3 h, 50 °C

Reference

Benzimidazole derivatives as inhibitors of PAD4 and their preparation

, World Intellectual Property Organization, , ,

Production Method 14

503000-87-1

95652-77-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  12 h, rt → 150 °C

Reference

Preparation of heteroaryl compounds as SSAO/VAP-1 inhibitors

, China, , ,

Production Method 15

65515-28-8

95652-77-0

Reaction Conditions

1.1 Solvents: Methanol ;  20 °C; 3 h, 20 °C

Reference

Salt type, crystal form, and use of fused pyridinone compound

, World Intellectual Property Organization, , ,

Production Method 16

65515-28-8

95652-77-0

Reaction Conditions

1.1 Solvents: Methanol ;  rt; 3 h, 20 °C

Reference

Fused pyridone compound, preparation method and application

, World Intellectual Property Organization, , ,

Production Method 17

18107-18-1

503000-87-1

95652-77-0

Reaction Conditions

1.1 Solvents: Methanol ,  Dichloromethane ;  12 h, 23 °C

Reference

Preparation of 2-amino-N-phenylnicotinamides as NAV1.8 inhibitors

, World Intellectual Property Organization, , ,

Production Method 18

18107-18-1

503000-87-1

95652-77-0

Reaction Conditions

1.1 Solvents: Methanol ,  Dichloromethane ;  0 °C; 10 min, 0 °C
1.2 Reagents: Acetic acid

Reference

Pyrazole, triazole and tetrazole orexin receptor antagonists

, World Intellectual Property Organization, , ,

Production Method 19

1073230-28-0

95652-77-0

Reaction Conditions

1.1 1 h, reflux; 12 h, rt

Reference

Preparation of novel N-(4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl)carbonyl substituted amino acid derivatives as HIF prolyl hydroxylase inhibitors for treating anemia

, World Intellectual Property Organization, , ,

Production Method 20

503000-87-1

95652-77-0

Reaction Conditions

1.1 Reagents: Thionyl chloride ;  overnight, reflux; reflux → rt
1.2 3 h, reflux; reflux → rt

Reference

Preparation of azaquinolone-based compounds exhibiting prolyl hydroxylase inhibitory activity

, World Intellectual Property Organization, , ,

methyl 2-chloro-6-methoxy-pyridine-3-carboxylate Raw materials

• Methyl 2,6-dichloronicotinate
• 2-chloro-6-hydroxypyridine-3-carboxylic acid
• 2-chloro-6-methoxypyridine-3-carbonyl chloride
• (diazomethyl)trimethylsilane
• 2-Chloro-6-methoxynicotinic acid

methyl 2-chloro-6-methoxy-pyridine-3-carboxylate Preparation Products

• methyl 2-chloro-6-methoxy-pyridine-3-carboxylate (95652-77-0)

• 1. Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles via redox condensation of o-nitrophenols with acetophenones and methylquinolines?
  Thi Thu Tram Nguyen,Thanh Binh Nguyen Org. Biomol. Chem., 2021,19, 6015-6020
• 2. Empowering microfluidics by micro-3D printing and solution-based mineral coating?
  Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun Zhang Soft Matter, 2020,16, 6841-6849
• 3. Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond?
  Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
• 4. Evolution and characterization of a benzylguanine-binding RNA aptamer?
  J. Xu,T. J. Carrocci,A. A. Hoskins Chem. Commun., 2016,52, 549-552
• 5. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxylic acids and derivatives Pyridinecarboxylic acids

Methyl 2-Chloro-6-methoxy-pyridine-3-carboxylate (CAS No. 95652-77-0): An Overview

Methyl 2-chloro-6-methoxy-pyridine-3-carboxylate (CAS No. 95652-77-0) is a versatile compound with significant applications in the fields of chemistry, biology, and pharmaceuticals. This compound, often referred to by its CAS number for identification, is a methyl ester derivative of a substituted pyridine carboxylic acid. Its unique chemical structure and properties make it an important intermediate in the synthesis of various bioactive molecules and pharmaceuticals.

The chemical formula of methyl 2-chloro-6-methoxy-pyridine-3-carboxylate is C₁₀H₁₀ClNO₃. It is characterized by a pyridine ring with a chlorine atom at the 2-position, a methoxy group at the 6-position, and a carboxylate group at the 3-position, which is esterified with methanol. This molecular structure confers specific reactivity and stability properties that are crucial for its applications in synthetic chemistry and drug development.

In recent years, significant research has been conducted to explore the potential of methyl 2-chloro-6-methoxy-pyridine-3-carboxylate in various fields. One of the key areas of interest is its use as an intermediate in the synthesis of agrochemicals and pharmaceuticals. The chlorine and methoxy substituents on the pyridine ring provide functional handles that can be readily modified through various chemical reactions, making it a valuable building block for the synthesis of more complex molecules.

A notable application of methyl 2-chloro-6-methoxy-pyridine-3-carboxylate is in the development of novel pesticides. The compound's ability to undergo selective functionalization reactions allows chemists to design and synthesize compounds with enhanced biological activity and reduced environmental impact. For instance, recent studies have shown that derivatives of this compound exhibit potent insecticidal properties against a range of pests, making them promising candidates for the next generation of pest control agents.

In the pharmaceutical industry, methyl 2-chloro-6-methoxy-pyridine-3-carboxylate has gained attention as a key intermediate in the synthesis of drugs targeting various diseases. The pyridine scaffold is known for its ability to modulate biological pathways and interact with specific receptors, making it an attractive platform for drug discovery. Research has demonstrated that derivatives of this compound can exhibit anti-inflammatory, antiviral, and anticancer activities, depending on their structural modifications.

One specific example is the use of methyl 2-chloro-6-methoxy-pyridine-3-carboxylate in the synthesis of inhibitors for kinases, which are enzymes involved in many cellular processes including cell growth and division. Kinase inhibitors have shown promise in treating cancers by blocking the uncontrolled cell proliferation characteristic of these diseases. By modifying the chlorine and methoxy groups on the pyridine ring, researchers have developed compounds with high selectivity and potency against specific kinases.

The synthetic versatility of methyl 2-chloro-6-methoxy-pyridine-3-carboxylate also extends to its use in combinatorial chemistry. Combinatorial approaches involve generating large libraries of compounds by systematically varying functional groups on a common scaffold. This method has been instrumental in identifying lead compounds for drug development. The ability to easily modify the chlorine and methoxy substituents on the pyridine ring makes methyl 2-chloro-6-methoxy-pyridine-3-carboxylate an ideal starting material for such combinatorial strategies.

Beyond its applications in agrochemicals and pharmaceuticals, methyl 2-chloro-6-methoxy-pyridine-3-carboxylate has also been explored for its potential in materials science. The unique electronic properties of pyridine derivatives make them suitable for use in organic electronics, such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). Recent studies have shown that derivatives of this compound can enhance the performance of these devices by improving charge transport properties and stability.

In conclusion, methyl 2-chloro-6-methoxy-pyridine-3-carboxylate (CAS No. 95652-77-0) is a multifaceted compound with a wide range of applications across multiple disciplines. Its chemical structure provides a robust platform for synthetic modifications, making it an invaluable intermediate in the development of new agrochemicals, pharmaceuticals, and advanced materials. As research continues to uncover new possibilities for this compound, its importance in modern chemistry and related fields is likely to grow even further.

• 921599-93-1(3-Pyridinecarboxylic acid, 2-chloro-, 2-pyridinyl ester)
• 95652-80-5(2-Chloro-6-methoxynicotinaldehyde)
• 1246765-45-6(Methyl 6-chloro-2-ethoxynicotinate)
• 1221172-04-8(2-Chloro-6-(trifluoromethoxy)nicotinic acid)
• 959616-64-9(methyl 2-chloro-5-fluoro-6-methoxypyridine-3-carboxylate)
• 503000-87-1(2-Chloro-6-methoxynicotinic acid)
• 106719-00-0(3,4-Pyridinedicarboxylic acid, 6-chloro-2-methoxy-, dimethyl ester)
• 106718-97-2(Ethyl 6-chloro-2-methoxynicotinate)
• 65515-32-4(methyl 6-chloro-2-methoxypyridine-3-carboxylate)
• 42521-10-8(methyl 2-chloro-6-methoxypyridine-4-carboxylate)