With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.174669-74-0, name is 2-Fluoropyridin-3-ol, molecular formula is C5H4FNO, molecular weight is 113.09, as common compound, the synthetic route is as follows.Quality Control of 2-Fluoropyridin-3-ol
A solution comprising 2,3,4,6-Tetra-O- acetyl-a-D-galactopyranosyl bromide 3 (1 .0 g, 2.4 mmol), Ag2C03 (0.74 g, 2.7 mmol), MS- 4A (5 g) and 2-fluoro-pyridin-3-ol 5 (0.33 g, 2.9 mmol) in anhydrous DCM (15 mL ) is stirred overnight, in the dark, at room temperature, under an argon atmosphere. TLC analysis indicated the complete consumption of the starting bromide and the formation of a new nonpolar product. The solution is filtered through a celite, which was rinsed with DCM (3 x 10 mL ). After removing the solvent under reduced pressure, the crude residue is purified directly using silica gel column chromatography, using an increasing gradient of EtOAc in PE. The product afforded is a colorless solid (0.51 g, 51 %). (0101) [0074] TLC: Rf = 0.5 (EtOAc: PE = 1 : 1 ); 1H NMR (600 MHz, Chloroform-d) delta 7.94 (d, J= 4.6 Hz, 1 H, ArH), 7.58 (t, J= 7.8 Hz, 1 H, ArH), 7.13 (dd, J= 7.8, 4.8 Hz, 1 H, ArH), 5.50 (dd, J= 10.5, 7.9 Hz, 1 H), 5.45 (d, J= 3.4 Hz, 1 H), 5.10 (dd, J= 10.5, 3.4 Hz, 1 H), 4.96 (d, J= 7.9 Hz, 1 H), 4.22 (dd, J= 1 1.4, 6.8 Hz, 1 H), 4.15 (dd, J= 1 1 .4, 6.3 Hz, 1 H), 4.01 (td, J = 6.8, 1 .1 Hz, 1 H), 2.19 (s, 3H, OAc), 2.1 1 (s, 3H, OAc), 2.04 (s, 3H, OAc), 2.02 (s, 3H, OAc); 13C NMR (151 MHz, CDCI3) delta 170.26 (COquart), 170.13 (COquart), 170.04 (COquart), 169.44 (COquart), 154.75 (d, J= 239.9 Hz), 141 .59 (d, J= 13.4 Hz, ArC), 139.49 (d, J= 25.5 Hz, ArC), 130.22 (d, J = 3.5 Hz, ArC), 121.85 (d, J = 4.3 Hz, ArC), 121.23 (CH), 101.12 (CH), 71.38 (CH), 70.5 (CH), 68.29 (CH), 66.70 (CH), 61.17 (CH2), 21.03 (OAc), 20.63 (OAc), 20.61 (OAc), 20.55 (OAc).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,174669-74-0, 2-Fluoropyridin-3-ol, and friends who are interested can also refer to it.
Reference:
Patent; EBERHARD KARLS UNIVERSITAET TUEBINGEN MEDIZINISCHE FAKULTAET; COTTON, Jonathan; KUEHN, Anna; MAURER, Andreas; PICHLER, Bernd; SCHULZE-OSTHOFF, Klaus; FUCHS, Kerstin; KRUEGER, Marcel Andre; ZENDER, Lars; (42 pag.)WO2018/153966; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem