344-14-9, name is Dimethyl 2-fluoromalonate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C5H7FO4
Intermediate 345 A: Methyl 2-fluoropent-4-ynoate In a 20 mL microwave vial, a mixture of dimethyl 2-fluoromalonate (900 mg, 6.0 mmol) in DMA (5 mL) at room temperature with stirring, was treated with the slow addition of sodium hydride (240 mg, 6 mmol, 60%) at 0 C. The mixture was stirred for 10 minutes, then added 3-bromoprop-l-yne (743 mg, 5.0 mmol, 80% in xylenes) and the mixture was stirred vigorously at 25 C for 1.5 hours. TLC shows consumption of the bromide. A syringe needle was placed through the septum to allow gases to vent, then the mixture was heated at 90 C for 20 hours. The reaction was quenched with the careful addition under nitrogen of saturated NH4CI solution (0.5 mL), and extracted with ethyl acetate (3 X 25 mL). The combined extracts were dried over Na2S04 to give a few ml of a brown oil as crude product. The crude product was dissolved in ethyl acetate and rinsed 3 times with 10% LiCl to remove DMA. The organic layer was dried over sodium sulfate, and then concentrated to give an amber oil which was purified over silica gel in 9: 1 to 3 : 1 hexanes/EtOAc to afford methyl 2-fluoropent-4-ynoate (600 mg, 69% yield). NMR (400MHz, CHLOROFORM-d) delta 3.84 (s, 3H), 2.92-2.74 (m, 2H), 2.14-2.00 (m, 1H), 1.27 (d, J=5.3 Hz, 1H). LCMS 130.2 (M+H)+.
The synthetic route of 344-14-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GARDNER, Daniel S.; SANTELLA, Joseph B.; PAIDI, Venkatram Reddy; WU, Hong; DUNCIA, John V.; NAIR, Satheesh Kesavan; HYNES, John; (300 pag.)WO2016/210034; (2016); A1;,
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