Electric Literature of 1256808-59-9, 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.1256808-59-9, name is 5-Fluoro-3-methylpicolinic acid, molecular formula is C7H6FNO2, molecular weight is 155.13, as common compound, the synthetic route is as follows.
To a solution of tert-butyl ((3aR,4R,8S)-4-(6-amino-3-fluoropyridin-2-yl)-4,7,7- trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H-isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int- 39BA, 150 mg, 0.35 mmol) in THF (20 mL) was added 5-fluoro-3-methylpicolinic acid (82 mg, 0.53 mmol) followed by T3P (1.1 g, 1.75 mmol, 50% in ethyl acetate), and diisopropylethylamine (267 mg, 2.1 mmol). The reaction was stirred at 70 C for 4 h. After that, the reaction mixture was diluted with aqueous saturated sodium hydrogencarbonate solution (20 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a crude product. The crude was purified by column chromatography (silica gel, eluting with petroleum ether / ethyl acetate 1: 1) to yield, after drying in vacuo, the title compound as a yellow solid (130 mg, 66% yield). XH NMR (CDC13, 400 MHz): delta 0.81-0.91 (m, 3 H), 1.49-1.59 (m, 9 H), 1.67- 1.76 (m, 6 H), 2.08-2.22 (m, 1 H), 2.52-2.64 (m, 1 H), 2.76-2.87 (m, 3 H), 3.71-3.87 (m, 2 H), 5.21 (dd, / = 7.1, 11.0 Hz, 1 H), 7.37 (dd, / = 2.3, 8.8 Hz, 1 H), 7.48-7.57 (m, 1 H), 8.37 (d, / = 2.5 Hz, 1 H), 8.44 (dd, / = 3.0, 8.9 Hz, 1 H), 10.46 (s, 1 H), 11.00 (br s, 1 H). MS (ES+) mJz 563.2 [M+H] .
Statistics shows that 1256808-59-9 is playing an increasingly important role. we look forward to future research findings about 5-Fluoro-3-methylpicolinic acid.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem