Reference of 460-37-7, These common heterocyclic compound, 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, 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 50-mL round bottom flask equipped with a magnetic stir bar, a temperature probe, and a reflux condenser was charged S-(3-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)amino)-3-oxopropyl) ethanethioate (1.0 g, 3 mmol, 96% HPLC purity) and MeOH (30 mL). To the suspension was added NaOMe (0.497 g, 9 0 mmol) and the reaction mixture was stirred at room temperature for 30 min, at which point HPLC analysis indicated that <0.3% of S-(3-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)amino)-3-oxopropyl) ethanethioate remained. 1,1,1-Trifluoro-3-iodopropane (2.06 g, 9. 0 mmol) was added and the mixture was heated at 50 C. for 30 min, at which point HPLC analysis indicated that <1.5% of thiol intermediate remained. The reaction mixture was cooled to room temperature, filtered, and the filter cake washed with MeOH (10 mL) The filtrate was concentrated to afford crude product as an off-white solid (2.0 g, 90% HPLC purity), which was purified by flash column chromatography (0-100% EtOAc/hexanes) to afford the desired product as a white solid (1.0 g, 86%, 98.2% HPLC purity). mp 111-114 C. 1H NMR (400 MHz, CDCl3): 8.97 (s, 1H), 8.63 (s, 1H), 8.54 (d, J=4.6 Hz, 1H), 7.97 (d, J=9.4 Hz, 1H), 7.64 (s, 1H), 7.39 (dd, J=8.3, 4.8 Hz, 1H), 2.95 (t, J=6.8 Hz, 2H), 2.75 (m, 4H), 2.32-2.50 (m, 2H). 13C NMR (101 MHz, CDCl3): 168.3, 147.9, 140.1, 136.1, 132.5, 127.4, 125.9, 124.7, 124.1, 120.0, 36.5, 34.7 (q, J=29 Hz), 27.6, 24.6. ESIMS m/z 378.9 ([M+H]+).
The synthetic route of 460-37-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Dow AgroSciences LLC; YANG, Qiang; LORSBACH, Beth; NIYAZ, Noormohamed M.; BUYSSE, Ann M.; WALSH, Martin J.; Zhang, Yu; TRULLINGER, Tony K.; MOLITOR, Erich J.; CANTURK, Belgin; HAO, Yan; KISTER, Jeremy; (23 pag.)US2018/186753; (2018); A1;,
Iodide – Wikipedia,
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