Methyl 5-fluoropicolinate Chemical Properties

Boiling point:

217.2±20.0 °C(Predicted)

Density 

1.243±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

-0.73±0.10(Predicted)

form 

solid

color 

Off-white

InChI

InChI=1S/C7H6FNO2/c1-11-7(10)6-3-2-5(8)4-9-6/h2-4H,1H3

InChIKey

KCMBKUFSDZMQEM-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC=C(F)C=C1

Safety Information

HS Code 

2933399990

Methyl 5-fluoropicolinate Usage And Synthesis

Uses

Methyl 5-fluoropicolinate is a fluoroorganic heterocyclic compound that can be used in the preparation of BTK inhibitors or degradation agents for the treatment of BTK-related diseases such as tumours or autoimmune system disorders.

Synthesis

General procedure for the synthesis of methyl 5-fluoropyridinecarboxylate: 5 g of 5-fluoropyridine-2-carboxylic acid was added to 50 mL of methanol and 2.7 mL of thionyl chloride was added slowly and dropwise. The reaction mixture was transferred to a sealed microwave reaction flask and the reaction was stirred at 65 °C for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in a solvent mixture of dichloromethane and methanol and filtered through a silica gel column. The filtrate was collected and concentrated under reduced pressure to give 5.9 g of the target compound, methyl 5-fluoropyridinecarboxylate. Thin layer chromatography showed an Rf value of 0.77 (Method K). Mass spectrometry analysis showed a molecular ion peak (M + H)+ of 156.

References

[1] Patent: WO2013/79460, 2013, A1. Location in patent: Page/Page column 46
[2] Patent: US2013/137688, 2013, A1. Location in patent: Paragraph 0239; 0240; 0241
[3] Patent: CN108003161, 2018, A. Location in patent: Paragraph 0628; 0630-0632

Methyl 5-fluoropicolinate(107504-07-4)Related Product Information

• 2-Pyridinecarboxylic acid, 4-bromo-5-chloro-, methyl ester
• 2-Pyridinecarboxylic acid, 4-chloro-5-(1,3-dioxolan-2-yl)-
• 2-Pyridinecarboxamide,5-fluoro-(9CI)
• 5-Fluoro-2-forMylpyridine
• METHYL 5-FLUOROPYRIDINE-3-CARBOXYLATE
• 3-FLUORO-5-FORMYLPYRIDINE
• 3-FLUORO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE