Discovery of 4-Fluoro-1H-pyrazole

According to the analysis of related databases, 35277-02-2, the application of this compound in the production field has become more and more popular.

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 35277-02-2 as follows. 35277-02-2

(5)-3-(4-Fluoro- lH-pyrazol- l-yl)-2-hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)- propanamide (C14H12F4N4O4) (1046) (0902) 1046 [00415] To a dry, nitrogen-purged 100 mL round-bottom flask equipped with a dropping funnel under argon atmosphere containing 4-fluoro-lH-pyrazole (691 mg, 8.03 mmol), NaH of 60% dispersion in mineral oil (674 mg, 16.9 mmol) was added in 60 mL of anhydrous THF solvent at ice- water bath. The mixture was stirred 30 min at the ice- water bath. Into the flask through dropping funnel, a solution of ( ?)-3-bromo-2-hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide (2.98 g, 8.03 mmol) in 10 mL of anhydrous THF was added under argon atmosphere at the ice-water bath, and stirred overnight at RT. After adding 1 mL of H2O, the reaction mixture was condensed under reduced pressure, and then dispersed into 50 mL of EtOAc, washed with 50 mL (x 2) water, evaporated, dried over anhydrous MgS04, and evaporated to dryness. The mixture was purified with flash column chromatography using as an eluent EtOAc/hexane in a 1:2 ratio to produce the titled compound (2.01 g, 67%) as yellow solid. (0903) [00416] Compound 1046 was characterized as follows: NMR (400 MHz, CDC13) delta 9.14 (bs, 1H, NH), 8.01 (s, 1Eta), 7.97-7.91 (m, 2Eta), 7.38 (d, = 3.6 Hz, 1H), 7.35 (d, = 4.4 Hz, 1H), 5.95 (s, 1H, OH), 4.56 (d, = 14.0 Hz, 1H), 4.17 (d, = 14.0 Hz, 1H), 1.48 (s, 3H); 19F NMR (CDCI3 decoupled) delta -60.13, -176.47; MS (ESI) mJz 375.08 [M – H] ~; 377.22 [M + H] +; 399.04 [M + Na] +.

According to the analysis of related databases, 35277-02-2, the application of this compound in the production field has become more and more popular.