Synthetic Route of 113209-90-8 ,Some common heterocyclic compound, 113209-90-8, molecular formula is C6H5ClFNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
A mixture of 6′-[3-(dimethylamino)-1-pyrrolidinyl]-4-hydroxy-2/-/-1 ,3′-bipyridin-2-one (150 mg, 0.499 mmol) and triphenylphosphine (327 mg, 1.249 mmol) was treated with (4-chloro-5-fluoro-2-pyridinyl)methanol (81 mg, 0.499 mmol) dissolved in dichloromethane (5 ml). Bis(1 ,1-dimethylethyl) (E)-1 ,2-diazenedicarboxylate (287 mg, 1.249 mmol) was added in two portions, and the reaction mixture was stirred at 250C for 2 h then concentrated under a stream of nitrogen gas. Purification by reverse phase HPLC (1 to 50% gradient) and concentration of the fractions containing product provided a residue. The residue was treated with aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to provide the title compound as a white solid (1 14 mg, 51 %): 1H NMR (400 MHz, CDCI3) delta ppm 8.46 (s, 1 H), 8.06 (d, J = 2.7 Hz, 1 H), 7.56-7.48 (m, 2 H), 7.21 (d, J = 7.6 Hz, 1 H), 6.43 (d, J = 9.0 Hz, 1 H), 6.09 (dd, J = 7.4, 2.5 Hz, 1 H), 5.98 (d, J = 2.7 Hz, 1 H), 5.10 (s, 2 H), 3.95-3.84 (m, 1 H), 3.77-3.65 (br m, 2H), 3.55-3.22 (br m, 2 H), 2.60 (br s, 6 H), 2.47-2.29 (br m, 2 H); ES-LCMS m/z 444 {M+H)+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113209-90-8, its application will become more common.
Reference:
Patent; GLAXO GROUP LIMITED; WO2009/76387; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem