Reference of 64591-03-3, These common heterocyclic compound, 64591-03-3, name is 2,5-Dibromo-1H-imidazole, 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.
General procedure: To a stuffed solution of 2,4-dibromothiazole (2) (4 mmol) in dimethylformamide (DMF) (15 mL), the coffesponding amine (1) (4 mmol) and diisopropylethylamine (DIPEA) (1.55 g, 2 mL, 12 mmol) were added under a stream of nitrogen.The reaction mixture was stirred at 80C for 4-10 h (monitored by Thin-layer chromatography (TLC)), then cooled to room temperature (rt), quenched with cold water (H20) (50 mL) and extracted with ethyl acetate (EtOAc) (3×30 mL). The combined organic layer was washed with H20 (2×10 mL), dried over sodium sulfate and concentrated to give the crude compound 3. The resulting product 3, the corresponding imidazole 4 (12 mmol),palladium(II)bis(triphenylphosphine) diacetate (Pd(OAc)2(PPh3)2) (0.1 mmol) and toluene (50 mL) were refluxed for 24 h. After cooling, the organic solvent was removed under vacuum. The resulting residue was purified by preparative high-performance liquid chromatography (HPLC) (EtOAc – Hexane (1:5) as eluent) to give the final product 5 as a solid. It was additionally purified by reverse phase HPLC (gradient acetonitrile (MeCN) – H20, 20 to 80% of MeCN aseluent). A compound of formula S are examples 1-15, 17-22, 24-40, 42-50 and 52-62.
The synthetic route of 64591-03-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; THE UNIVERSITY OF BRITISH COLUMBIA; BAN, Fuqiang; DALAL, Kush; FLOHR, Alexander; LEBLANC, Eric J. J.; LI, Huifang; RENNIE, Paul S.; TCHERKASSOV, Artem; (57 pag.)WO2018/114781; (2018); A1;,
Imidazole – Wikipedia,
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