Synthetic Route of 25016-11-9, These common heterocyclic compound, 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, 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.
To a solution of 1-(methylsulfonyl)-5,6-dihydropyridin-2(11])-one (200 mg, 1.14 mmol, 1.0 eq), diethyl phosphorochloridate (197 mg, 1.14 mmol, 1 eq) and 1-methyl-1H-pyrazole-4- carbaldehyde (100 mg, 0.91 mmol, 0.8 eq) in THF (10 mL) at 0C was added LiHIVIDS 1M in THF (2.5 mL, 2.50 mmol, 2.0 eq). The reaction mixture was stirred at 0C for lh. Progress ofreaction was monitored by TLC. Reaction mixture was quenched by saturated ammonium chloride solution 20 mL and extracted with ethyl acetate (3 x 50 mL). Combined organic layer was washed with brine solution (50 mL) and dried over anhydrous Na2SO4. Removal of solvent under reduced pressure gave the crude which was purified by flash column chromatograpy (0-70% EtOAc-hexane) as eluent to 1- { [(E)-2-( 1-methyl- 1H-pyrazol-4-yl)ethenyl] sulfonyl } -5,6-dihydropyridin-2(11])-one (90 mg, 29.50%).LCMS: 268[M+1]1H NMR (400IVIHz, CDC13) (57.69 (s, 1 H), 7.59 (s, 1 H), 7.55 (d, 1 H), 6.91 (d, 1 H), 6.81 -6.86 (m, 1H), 5.97 (d, 1 H), 3.96 (t, 2 H), 3.92 (s, 3 H), 2.51 – 2.57 (m, 2 H),
The synthetic route of 25016-11-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; AURANSA INC.; PROTTER, Andrew, Asher; GREEN, Michael, John; CHANG, Hak, Jin; PHAM, Son, Minh; CHAKRAVARTY, Sarvajit; LUEDTKE, Gregory, R.; (254 pag.)WO2019/103897; (2019); A1;,
Pyrazole – Wikipedia,
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