Some common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, molecular formula is C4H3F3N2, 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. Computed Properties of C4H3F3N2
To a solution of a tert-butyl 4-(bromomethyl)piperidine-1-carboxylate (0.5 g, 1.8 mmol, CASRN: 15 8407-04-6) in dry DMF (4 mL) was added 4-(trifluoromethyl)-1H-imidazole (293 mg,2.16 mmol) and Cs2CO3 (1.17 g, 3.59 mmol). The reaction mixture was then stirred at 80 C for14 h. Insolubles were removed by filtration, and the filtrate was concentrated in vacuo. Thecrude residue was suspended in DCM and filtered through a pad of Celite to give a yellow oil,which was purified by flash chromatography with a 5i02 column, using an eluent mixture of nheptane and EtOAc (10% to 90%). This yielded the first fraction (301 mg) of the desired product as a colorless oil, and a second fraction (261 mg) of a mixture of the desired product with impurities. The second fraction was submitted for SFC purification, and the purified product was combined with the first fraction to yield 430 mg of the desired product as a colorless oil. MS(ESI): m/z = 334.2 [M+H].
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33468-69-8, its application will become more common.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ANSELM, Lilli; BENZ, Joerg; GRETHER, Uwe; GROEBKE ZBINDEN, Katrin; HEER, Dominik; HORNSPERGER, Benoit; KROLL, Carsten; KUHN, Bernd; O`HARA, Fionn; RICHTER, Hans; (268 pag.)WO2020/35425; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem