Synthetic Route of 52222-73-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.
To a room temperature solution of C5 (100 mg, 0.208 mmol) in N,N-dimethylformamide (2 mL) was added cesium carbonate (170 mg, 0.522 mmol), followed by 4-(trifluoromethyl)-1H-pyrazole (42.5 mg, 0.312 mmol), and the reaction mixture was stirred at 80 C. overnight. It was then partitioned between water and ethyl acetate, and the aqueous layer was extracted with ethyl acetate (3*15 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 0% to 25% ethyl acetate in heptane) provided the product as an oil. Yield: 71 mg, 0.13 mmol, 62%. LCMS m/z 536.4 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.74 (s, 1H), 7.69 (s, 1H), 7.25 (br d, J=8.6 Hz, 2H), 6.88 (br d, J=8.6 Hz, 2H), 5.54-5.44 (m, 1H), 4.78 (quint, J=8.4 Hz, 1H), 4.51 (AB quartet, JAB=11.7 Hz, DeltanuAB=28.5 Hz, 2H), 3.81 (s, 3H), 3.76 (dd, half of ABX pattern, J=11.3, 3.9 Hz, 1H), 3.69 (br dd, half of ABX pattern, J=10.9, 7.0 Hz, 1H), 3.55-3.47 (br m, 2H), 3.47-3.38 (br m, 2H), 2.52-2.42 (m, 2H), 2.38 (dd, half of ABX pattern, J=12.5, 8.6 Hz, 2H), 1.76-1.62 (br m, 4H).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(Trifluoromethyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; PFIZER INC.; BRODNEY, MICHAEL AARON; BUTLER, CHRISTOPHER RYAN; MCALLISTER, LAURA ANN; HELAL, CHRISTOPHER JOHN; O’NEIL, STEVEN VICTOR; VERHOEST, PATRICK ROBERT; (103 pag.)US2018/208607; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics