Electric Literature of 1402838-08-7,Some common heterocyclic compound, 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, molecular formula is C29H22N2O, 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.
A mixture of 10b (210 mg, 1.180 mmol) , 2-hydroxyisoindoline-1, 3-dione (38 mg, 0.233 mmol) , Bis (acetylacetonato) cobalt (30 mg, 0.117 mmol) in HOAc (5 mL) was stirred under oxygen atmosphere at 75 for 6 h. The reaction mixture was concentrated to dryness under reduced pressure. The residue was diluted with EtOAc (10 mL) and the insoluble solid was filtered off. The filtrate was concentrated in vacuo to afford a crude mixture of 14b and 14c (160 mg) as slight brown oil, which was used for the next step without further purification. To a stirred mixture of compound 10a (150 mg, 0.362 mmol) and compounds 14b and 14c (70 mg, 0.362 mmol) in anhydrous THF (10mL) was added dropwise a solution of EtONa (21in EtOH, 152mg, 0.471mmol) at room temperature. The reaction mixture was stirred at room temperature for 1.5 h. After the mixture was concentrated to dryness under reduced pressure, the residue was diluted with NH4Cl solution (10mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was dissolved in MeOH (8 mL) . To this solution was added HOAc (2 mL) , and the reaction mixture was stirred at 60 for 2 h. The mixture was concentrated in vacuo to give a residue, which was diluted with NaHCO3saturated solution (10 mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was purified by preparative TLC (EtOAc) to afford compound 14d (70 mg, 55yield) , MS 349.2 [M+H]+, and 14e (40 mg, 31yield) as a light yellow solid, MS Found 365.2 [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 2-(1-Trityl-4-imidazolyl)benzaldehyde, its application will become more common.
Reference:
Patent; HANGZHOU INNOGATE PHARMA CO., LTD.; ZHANG, Hancheng; LIU, Shifeng; (53 pag.)WO2016/165613; (2016); A1;,
Imidazole – Wikipedia,
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