Application of 39070-14-9, A common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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.
300 mg of 3 (1 eq., 0.55 mmol), 86 mg of 1 (1 eq., 0.55 mmol),326 mg of Cu(OAc)2·H2O, 18 mg of potassium iodide (0.2 eq.,0.11 mmol) and 6 mg of Pd(OAc)2 were dissolved in 3 mL of dimethylsulfoxide and 12 mL acetonitrile. The reaction vessel was set under anatmospheric pressure of carbon monoxide (CAUTION: highly toxic) andshortly warmed with a hot water bath (40 C). After 1 h the reactionmixture was taken up in EtOAc and washed with sat. NaHCO3 andwater. The combined aqueous solutions were washed with EtOAc andthe combined organic solutions were washed with brine, dried overMgSO4 and the solvent was removed under reduced pressure. The crudeproduct was dried in vacuo overnight. Purification was performed usingcolumn chromatography (EtOAc/petrol ether 9:1). Yield: 160 mg(40%). 1H NMR (500 MHz, DMSO-d6) delta 9.35 (s, 1H), 8.65 (s, 1H), 8.41(s, 1H), 8.23 (s, 2H), 7.84 (s, 1H), 7.54 (dd, J = 8.9, 5.0 Hz, 1H), 7.45(t, J = 8.7 Hz, 1H), 7.38 (s, 1H), 7.28 (s, 1H), 6.15 (d, J = 6.6 Hz, 1H),5.30 – 5.19 (m, 2H), 4.52 (t, J = 10.9 Hz, 1H), 3.96 (s, 3H), 3.10 (dd,J = 23.1, 11.6 Hz, 2H), 2.23 (d, J = 11.4 Hz, 2H), 2.15 – 2.06 (m, 2H),1.73 (d, J = 6.6 Hz, 3H), 1.43 (s, 9H) ppm. ESI-MS (M + Na): calc:755.19 found: 755.39.
The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Berger, Walter; Bielec, Bjoern; Heffeter, Petra; Keppler, Bernhard K.; Kowol, Christian R.; Schueffl, Hemma; Terenzi, Alessio; Bioorganic Chemistry; vol. 99; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem