Reference of 3718-04-5, A common heterocyclic compound, 3718-04-5, name is 5-Vinyl-1H-imidazole, molecular formula is C5H6N2, 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.
Example 35 (E)-2-(4-fluorophenyl)- 1 -methyl- 1 -(4-(2-( 1 -propyl- lH-imidazol-4-yl)vinyl)phenyl)- 1.2.3.4- tetrahvdroisoquinolin-6-ol To a 30 mL vial, 4-vinyl-lH-imidazole (400 mg, 4.25 mmol) was dissolved in THF (2 mL) and the solution was cooled to 0 C. The reaction vial was charged with 60% sodium hydride in mineral oil (170 mg, 4.25 mmol) and the reaction mixture stirred for 10 min at 0 C. To the mixture was added 1-iodopropane (0.415 mL, 4.25 mmol) and the reaction was stirred overnight at room temperature. The reaction was quenched with saturated ammonium chloride (15 mL) and diluted with dichloromethane (25 mL). The organic phases were combined, passed through a phase separator and concentrated to afford the crude product. The crude material was purified by column chromatography (1-10% dichloromethane/methanol) to afford a mixture of l-propyl-4-vinyl-lH-imidazole and l-propyl-5-vinyl-lH-imidazole (511 mg, 3.72: 1). l-propyl-4-vinyl-lH-imidazole: NMR (400 MHz, CHLOROFORM-^ delta 0.83 – 0.91 (m, 3 H), 1.66 – 1.82 (m, 2 H), 3.74 – 3.90 (m, 2 H), 5.11 (dd, J=11.12, 1.52 Hz, 1 H), 5.73 – 5.87 (m, 1 H), 6.52 (dd, J=17.18, 11.12 Hz, 1 H), 6.80 (s, 1 H), 7.58 (s, 1 H). l-propyl-5-vinyl-lH-imidazole: NMR (400 MHz, CHLOROFORM-^ delta 0.78 – 0.93 (m, 3 H), 1.63 – 1.82 (m, 2 H), 3.76 – 3.90 (m, 2 H), 5.22 (d, J=11.12 Hz, 1 H), 5.57 (d, J=17.18 Hz, 1 H), 6.41 (dd, J=17.43, 11.37 Hz, 1 H), 7.17 (s, 1 H), 7.63 (s, 1 H). To a microwave vial, l-(4-bromophenyl)-2-(4-fluorophenyl)-6-methoxy-l- methyl- 1, 2,3 ,4-tetrahydroisoquinoline (0.13 g, 0.305 mmol) was dissolved in DMF (2 mL) and triethylamine (213 mu^, 1.525 mmol). To the solution was added a mixture of 1 -propyl -4-vinyl- lH-imidazole and l-propyl-5 -vinyl- lH-imidazole (125 mg, 0.915 mmol) and Pd(PPh3)2Cl2 (0.032 g, 0.046 mmol). The system was flushed with nitrogen and heated at 150 C for 1 h under microwave radiation. The mixture was cooled to room temperature and quenched with saturated ammonium chloride. The reaction mixture was extracted with dichloromethane (3 x), the organic layers were combined, passed through a phase separator, and concentrated to give crude material. The crude material was purified by silica gel chromatography (0-75% ethyl acetate/heptanes) to afford mixture of two isomers (141 mg, 0.293 mmol, 96% yield). LC MS (m/z, MH+): 482.1.
The synthetic route of 3718-04-5 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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