107504-07-4

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.

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.

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[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