As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 174669-74-0, name is 2-Fluoropyridin-3-ol, molecular formula is C5H4FNO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Safety of 2-Fluoropyridin-3-ol
To a suspension of sodium hydride (0.129 g, 3.21 mmol) in DMF (10 mL) at 0 C was dropwise added a stuffing solution of 2-fluoropyridin-3-ol (0.363 g, 3.21 mmol) in DMF (5 mL), then followed by the dropwise addition of the solution of 2-(2-(2-(2- azidoethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (1.00 g, 2.68 mmol) in DMF (5 mL). The suspension was held at 0 C for 10 mm, then brought to ambient temperature for 1 hour, followed by additional heating at 60 C for 4 hours. The solvent was removed in vacuo. 100 ml of ethyl acetate was added followed by 3 separate wash extractions with concentrated brine solution. The organic layer was dried over sodium sulfate, filtered, and concentrated. The crude material was purified using flash chromatography (IscoCombiFlash – eluted with 10 – 50% EtOAc in Hex) to give a colorless oil. 3-(2-(2-(2-(2- azidoethoxy)ethoxy)ethoxy)ethoxy)-2-fluoropyridine (702 mg, 2.233 mmol, 83 % yield) was isolated as a clear oil. ?H NMR (400MHz, CHLOROFORM-d) oe 7.75 (dt, 1=4.9, 1.6 Hz, 1H), 7.33 (ddd, 1=10.0, 8.1, 1.5 Hz, 1H), 7.10 (ddd, 1=7.9, 4.9, 0.7 Hz, 1H), 4.30 – 4.16 (m, 2H),3.95 – 3.83 (m, 2H), 3.80 – 3.61 (m, 1OH), 3.38 (t, 1=5.1 Hz, 2H) 13C NMR (101MHz, CHLOROFORM-d) d 142.3, 137.7, 137.5, 123.4, 123.4, 121.7, 121.6, 77.3, 76.7, 70.9, 70.7, 70.6, 70.0, 69.4, 69.0, 50.6 19F NMR (400MHz, CHLOROFORM-d) oe -83.55. HRMS (ESI) Theory:C 1 3H20FN404+ mlz 315.464; found 315.1463.
With the rapid development of chemical substances, we look forward to future research findings about 174669-74-0.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MORIN, Paul, E.; DONNELLY, David; LIPOVSEK, Dasa; GOKEMEIJER, Jochem; JURE-KUNKEL, Maria, N.; FABRIZIO, David; WRIGHT, Martin, C.; DISCHINO, Douglas; BONACORSI, Samuel, J.; SMITH, Ralph, Adam; LAFONT, Virginie; (0 pag.)WO2016/86021; (2016); A1;,
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