Methyl 2-fluoro-6-methoxynicotinate

Base Information

• Chemical Name: Methyl 2-fluoro-6-methoxynicotinate
• CAS No.: 117671-03-1
• Molecular Formula: C₈H₈FNO₃
• Molecular Weight: 185.155
• DSSTox Substance ID: DTXSID50445326
• Nikkaji Number: J1.403.921J
• Wikidata: Q82263694
• Mol file: 117671-03-1.mol

Synonyms:methyl 2-fluoro-6-methoxynicotinate;117671-03-1;methyl 2-fluoro-6-methoxypyridine-3-carboxylate;3-Pyridinecarboxylic acid, 2-fluoro-6-methoxy-, methyl ester;DTXSID50445326;YLLWDQYTWVZRJD-UHFFFAOYSA-N;methyl2-fluoro-6-methoxynicotinate;MFCD11227195;AKOS006323923;AS-30958;CS-0062012;A846421;J-522018;2-Fluoro-6-methoxy-3-pyridinecarboxylic acid methyl ester;2-Fluoro-6-Methoxy-3-Pyridinecarboxylic Acid, Methyl Ester

Chemical Property of Methyl 2-fluoro-6-methoxynicotinate

Chemical Property:

• Melting Point: 81-82℃
• Boiling Point: 247.1±40.0 °C(Predicted)
• PKA: -4.30±0.10(Predicted)
• PSA: 48.42000
• Density: 1.244±0.06 g/cm3(Predicted)
• LogP: 1.01590
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 185.04882128
• Heavy Atom Count: 13
• Complexity: 188

Purity/Quality:

98% purity ^*data from raw suppliers

Methyl2-Fluoro-6-methoxynicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=NC(=C(C=C1)C(=O)OC)F

Technology Process of Methyl 2-fluoro-6-methoxynicotinate

There total 5 articles about Methyl 2-fluoro-6-methoxynicotinate 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:

6-methoxy-nicotinic acid methyl ester (26218-80-4) → methyl 2-fluoro-6-methoxypyridine-3-carboxylate (117671-03-1)

Guidance literature:

With silver(II) fluoride; In acetonitrile; for 1h; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/acs.orglett.8b03144

Reference yield:

6-methoxynicotinic acid (66572-55-2) → methyl 2-fluoro-6-methoxypyridine-3-carboxylate (117671-03-1)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2: triethylamine / 3 h

3: silver(II) fluoride / acetonitrile / 1 h / Inert atmosphere; Glovebox; Sealed tube

With oxalyl dichloride; silver(II) fluoride; triethylamine; N,N-dimethyl-formamide; In dichloromethane; acetonitrile;

DOI:10.1021/acs.orglett.8b03144

Reference yield:

6-methoxynicotinic acid chloride (193538-78-2) → methyl 2-fluoro-6-methoxypyridine-3-carboxylate (117671-03-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / 3 h

2: silver(II) fluoride / acetonitrile / 1 h / Inert atmosphere; Glovebox; Sealed tube

With silver(II) fluoride; triethylamine; In acetonitrile;

DOI:10.1021/acs.orglett.8b03144

upstream raw materials:

sodium methylate

methyl 2,6-difluoro-3-pyridinecarboxylate

2,6-difluoronicotinic acid

6-methoxy-nicotinic acid methyl ester

Downstream raw materials:

2-fluoro-6-methoxypyridine-3-carboxylic acid

methyl 2-fluoro-6-oxo-1,6-dihydropyridine-3-carboxylate

Refernces

• 1、 Hirokawa,Horikawa,Kato. "An efficient synthesis of 5-bromo-2-methoxy-6-methylaminopyridine-3-carboxylic acid". . p. 1847 - 1853. Retrieved 2007/10/03.