Application of 39070-14-9, These common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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.
Phenstatin (0.500 g, 1.57 mmol), (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (0.296 g, 1.89 mmol), and DIAD (0.40 mL, 2.04 mmol) were dissolved in CH2Cl2. Triphenylphosphine (0.825 g, 3.14 mmol) was added to the mixture, and the reaction mixture was stirred for 24 h. The reaction mixture was then evaporated under reduced pressure. Flash chromatography of the crude product using a prepacked 100 g silica column [eluents: solvent A: EtOAc; solvent B: hexanes; gradient, 17%A/83%B over 1.19 min (1 CV), 17%A/83%B 100%A/0%B over 8.33 min (7 CV), 100%A / 0%B over 5.95 min (5 CV); flow rate 100 mL/min; monitored at 254 and 280 nm] yielded (4-methoxy-3-((1-methyl-2-nitro-1H-imidazol-5-yl)methoxy)phenyl)(3,4,5-trimethoxyphenyl)methanone (31) as a pale yellow-white solid (0.346 g, 0.757 mmol, 48%) [0.284 g, 0.621 mmol, 39%, corrected for EtOAc].1H NMR (600 MHz, CDCl3) delta 7.62 (1H, d, J = 1.7 Hz), 7.52 (1H, dd, J = 8.3, 1.7 Hz), 7.24 (1H, s), 7.04 (2H, s), 6.97 (1H, d, J = 8.4 Hz), 5.18 (2H, s), 4.16 (3H, s), 3.97 (3H, s), 3.96 (3H, s), 3.91 (6H, s).13C NMR (151 MHz, CDCl3) delta 194.16, 153.97, 152.91, 146.74, 141.88, 132.92, 132.30, 130.43, 129.31, 127.00, 116.43, 110.61, 107.52, 99.98, 61.24, 61.01, 56.39, 56.05, 34.54.HRMS [M+Na]+: 480.1376 (calcd for [C22H23N3NaO8]+,480.1377).HPLC retention time (Method B): 4.66 min [100% at 254 nm].
The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Winn, Blake A.; Shi, Zhe; Carlson, Graham J.; Wang, Yifan; Nguyen, Benson L.; Kelly, Evan M.; Ross, R. David; Hamel, Ernest; Chaplin, David J.; Trawick, Mary L.; Pinney, Kevin G.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 636 – 641;,
Imidazole – Wikipedia,
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