With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.36958-61-9,5-(Bromomethyl)-3-methylisoxazole,as a common compound, the synthetic route is as follows.
tert-Butyl 2-[4-(5-chloro-2-fluorophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyl-1,2-oxazol-5-yl)propanoate (Racemate) To a solution of 900 mg (2.45 mmol) of tert-butyl [4-(5-chloro-2-fluorophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate in 18 ml of tetrahydrofuran under argon at -78 C. were added dropwise 3.06 ml (1.0 M in THF, 1.25 eq.) of lithium bis(trimethylsilyl)amide, and the mixture was stirred for 30 min. Subsequently, 635 mg (3.43 mmol, 1.4 eq.) of 5-(bromomethyl)-3-methyl-1,2-oxazole were added. The resulting reaction mixture was stirred at -78 C. for another 30 min and at RT for another 90 min. Saturated aqueous ammonium chloride solution was added to the reaction mixture. After phase separation, the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution. The organic phase was dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude product was then purified by means of normal phase chromatography (eluent: cyclohexane/ethyl acetate (0-38%) mixtures). Yield: 1.00 g (88% of theory) LC/MS [Method 1]: Rt=1.10 min; MS (ESIpos): m/z=463 (M+H)+, 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=7.54 (ddd, 1H), 7.48 (dd, 1H), 7.35 (t, 1H), 7.31 (s, 1H), 6.43 (s, 1H), 6.13 (s, 1H), 5.35 (dd, 1H), 3.68-3.56 (m, 2H), 3.55 (s, 3H), 2.16 (s, 3H), 1.40 (m, 9H).
36958-61-9, As the paragraph descriping shows that 36958-61-9 is playing an increasingly important role.
Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; STAMPFUss, Jan; (82 pag.)US2017/298052; (2017); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem