These common heterocyclic compound, 3718-04-5, name is 5-Vinyl-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. Computed Properties of C5H6N2
Example 20 (E)-2-(4-fluorophenyl)- 1 -methyl- 1 -(4-(2-(l -methyl- 1 H-imidazol-4-yl)vinyl)phenyl)- 1.2.3.4- tetrahvdroisoquinolin-6-ol and (EN)-2-(4-fluorophenvn-l-methyl-l-(4-(2-(l -methyl-lH-imidazol- 5-yl)vinyl)phenyl)-1.2.3.4-tetrahvdroisoquinolin-6-ol To a 30 mL vial, 4-vinyl-lH-imidazole (357 mg, 3.79 mmol) was dissolved in tetrahydrofuran (2 mL) and the solution was cooled to 0C. Sodium hydride (60% dispersion in mineral oil, 152 mg, 3.79 mmol) was added and the mixture was stirred for 10 min at 0C. The reaction mixture was charged with iodomethane (237 mu^, 3.79 mmol) and stirred overnight at room temperature. The reaction was quenched with saturated ammonium chloride (15 mL) and dichloromethane (25 mL) was added. The organic phase was collected, passed through a phase separator and concentrated to give crude product. Crude material was purified by silica gel chromatography (0-20% methanol/dichloromethane) to afford a mixture of 1 -methyl -4-vinyl-lH- imidazole and l-methyl-5 -vinyl- lH-imidazole (290 mg, 71% yield) as a yellow oil. NMR (400 MHz, CHLOROFORM-^ delta 3.51 (s, 3 H), 3.49 (s, 3 H), 4.97 (dd, J=11.12, 1.52 Hz, 1 H), 5.09 (dd, J=11.12, 1.01 Hz, 1 H), 5.44 (dd, J=17.68, 1.01 Hz, 1 H), 5.67 (dd, J=17.43, 1.77 Hz, 1 H), 6.25 – 6.49 (m, 2 H), 6.62 – 6.73 (m, 1 H), 7.04 (s, 1 H), 7.25 (d, J=7.58 Hz, 2 H).
The synthetic route of 5-Vinyl-1H-imidazole has been constantly updated, and we look forward to future research findings.
Reference:
Patent; NOVARTIS AG; BURKS, Heather Elizabeth; KARKI, Rajeshri Ganesh; KIRBY, Christina Ann; NUNEZ, Jill; PEUKERT, Stefan; SPRINGER, Clayton; SUN, Yingchuan; THOMSEN, Noel Marie-france; WO2015/92634; (2015); A1;,
Imidazole – Wikipedia,
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