Electric Literature of 1003-91-4, These common heterocyclic compound, 1003-91-4, name is 2,4,5-Tribromo-1-methylimidazole, 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 stirred suspension of NaH (68 mg, 1.71 mmol, 60% in mineral oil) in dry THF (5 mL) at 0 C was added a dry THF (6 mL) solution of 54 (268 mg, 1.14 mmol). After 30 min of stirring at 0 C, 2,4,5-tribromo-1-methyl-1H-imidazole [38] (399 mg, 1.10 mmol) was added. The reaction mixture was refluxed overnight, then cooled, and poured into ice water (?10 mL). The resulting mixture was extracted with EtOAc (2 * 10 mL). The combined organic phases were extracted with aq HCl solution (1M, 2 * 6 mL). The combined water phases were basified to pH 14 with a concentrated aq NaOH solution and extracted with EtOAc (3 * 10 mL). The combined organic phases were dried (MgSO4), filtered, and evaporated in vacuo. Purification by DCVC (DCM:MeOH:NH3/100:0:0 to 100:13:1) gave 1-((4,5-dibromo-1-methyl-1H-imidazol-2-yl)oxy-N,N-dimethyl-7-phenylheptan-3-amine as a yellow oil (155 mg, 29%). 1H NMR (CD3OD, 400 MHz) delta 7.26-7.20 (m, 3H), 7.18-7.10 (m, 3H), 4.41-4.29 (m, 2H), 3.36 (s, 3H), 2.62 (t, 3H, J = 7.5 Hz), 2.33 (s, 6H), 2.00 (dq, 1H, J = 14.4, 7.8 Hz), 1.81 (dq, 1H, J = 7.8, 6.8 Hz), 1.69-1.61 (m, 4H), 1.39-1.37 (m, 2H). 13C NMR (CD3OD, 101 MHz) delta 129.55 (2C), 129.44 (2C), 126.85, 110.88, 69.83, 62.27, 40.79 (2C), 36.88, 32.82, 31.03, 30.32, 27.78.
Statistics shows that 2,4,5-Tribromo-1-methylimidazole is playing an increasingly important role. we look forward to future research findings about 1003-91-4.
Reference:
Article; Bach, Tinna B.; Jensen, Anders A.; Petersen, Jette G.; S¡ãrensen, Troels E.; Della Volpe, Serena; Liu, Jun; Blaazer, Antoni R.; Van Muijlwijk-Koezen, Jacqueline E.; Balle, Thomas; Fr¡ãlund, Bente; European Journal of Medicinal Chemistry; vol. 102; (2015); p. 425 – 444;,
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