| Identification | Back Directory | [Name]
2-Pyridinecarboxylicacid,5-fluoro-,methylester(9CI) | [CAS]
107504-07-4 | [Synonyms]
Methyl 5-fluoropicolinate
Methyl 5-fluoropyridine-2-carboxylate
methyl 5-fluoro-2-pyridinecarboxylate
5-fluoro-2-pyridinecarboxylic acid methy
5-fluoro-2-pyridinecarboxylic acid methyl ester
5-Fluoropyridine-2-carboxylic acid methyl ester
2-PYRIDINECARBOXYLIC ACID, 5-FLUORO-, METHYL ESTER
2-Pyridinecarboxylicacid,5-fluoro-,methylester(9CI) | [Molecular Formula]
C7H6FNO2 | [MDL Number]
MFCD11845630 | [MOL File]
107504-07-4.mol | [Molecular Weight]
155.13 |
| Chemical Properties | Back Directory | [Boiling point ]
217.2±20.0 °C(Predicted) | [density ]
1.243±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
solid | [pka]
-0.73±0.10(Predicted) | [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 |
| Hazard Information | Back Directory | [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 |
|
|