2-chloro-5-fluoro-6-(Methyloxy)-3-pyridinecarboxylic acid

Base Information

• Chemical Name: 2-chloro-5-fluoro-6-(Methyloxy)-3-pyridinecarboxylic acid
• CAS No.: 943025-86-3
• Molecular Formula: C7H5ClFNO3
• Molecular Weight: 205.573
• Hs Code.: 2933399990
• Mol file: 943025-86-3.mol

Synonyms:2-chloro-5-fluoro-6-(methyloxy)-3-pyridinecarboxylic acid;2-chloro-5-fluoro-4-nitropyridine-1-oxide;

Chemical Property of 2-chloro-5-fluoro-6-(Methyloxy)-3-pyridinecarboxylic acid

Chemical Property:

• Melting Point: 164～166℃
• Boiling Point: 301.7±37.0 °C(Predicted)
• PKA: 2.02±0.32(Predicted)
• PSA: 59.42000
• Density: 1.518±0.06 g/cm3(Predicted)
• LogP: 1.58090
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloro-5-fluoro-6-methoxynicotinic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-chloro-5-fluoro-6-(Methyloxy)-3-pyridinecarboxylic acid

There total 1 articles about 2-chloro-5-fluoro-6-(Methyloxy)-3-pyridinecarboxylic acid 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: 97.4%

sodium methylate (124-41-4) + 2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid (82671-06-5) → 2-chloro-5-fluoro-6-methoxynicotinic acid (943025-86-3)

Guidance literature:

In methanol; for 4h; Reflux;

Reference yield:

2-chloro-5-fluoro-6-methoxynicotinic acid (943025-86-3) → 8-bromo-3,7-difluoro-2-(methyloxy)-1,5-naphthyridine (943025-91-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diphenyl phosphoryl azide; triethylamine / toluene / 2 h / 100 °C

2.1: cesium fluoride / bis(tri-t-butylphosphine)palladium⁽⁰⁾ / dioxane,1,4 / 100 °C

3.1: sodium hydrogencarbonate; Selectfluor / water; acetonitrile / 0.58 h / 0 - 20 °C

3.2: 0.17 h

4.1: toluene / 2 h / 40 °C

5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C

5.2: Alkaline conditions

6.1: phosphorus tribromide / N,N-dimethyl-formamide / 1.5 h

6.2: Alkaline conditions

With diphenyl phosphoryl azide; phosphorus tribromide; sodium hydrogencarbonate; Selectfluor; triethylamine; cesium fluoride; trifluoroacetic acid; bis(tri-t-butylphosphine)palladium⁽⁰⁾; In dioxane,1,4; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

2-chloro-5-fluoro-6-methoxynicotinic acid (943025-86-3) → (5-[6-fluoro-2,4-bis[(3S)-3-methylmorpholine-4-yl]pyrido[2,3-d]pyrimidin-7-yl]-2-methoxyphenyl)methanol

Guidance literature:

Multi-step reaction with 11 steps

1.1: thionyl chloride / 4 h / Reflux

1.2: 4 h / 20 °C

2.1: 3 h / 150 °C

3.1: trifluoroacetic acid / dichloromethane / 8 h / 20 °C

4.1: 6 h / 20 °C / Alkaline conditions

5.1: thionyl chloride / 4 h / Reflux

5.2: 1 h / 20 °C

6.1: toluene / 4 h / 115 °C

7.1: N-ethyl-N,N-diisopropylamine / toluene / 0.5 h / 70 °C / Inert atmosphere

7.2: 2.5 h / 100 °C / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C / Cooling with ice

9.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 48 h / 70 °C / Inert atmosphere

10.1: N-ethyl-N,N-diisopropylamine; phosphorus(V) oxybromide / toluene / 5 h / 100 °C / Inert atmosphere

11.1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / acetonitrile / 18 h / 90 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; phosphorus(V) oxybromide; In dichloromethane; N,N-dimethyl acetamide; toluene; acetonitrile;

upstream raw materials:

sodium methylate

2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid

Downstream raw materials:

8-bromo-3,7-difluoro-2-(methyloxy)-1,5-naphthyridine

Refernces

• 1、 -. "TRICYCLIC COMPOUNDS AS ANTIBACTERIALS". Page/Page column 56. . Retrieved 2008/12/08.