Reference of 17325-26-7, These common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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 solution of 5-fluoro-indan-1-ol (0.293 g, 1.925 mmol) and methyl 4- imidazolecarboxylate (CASNo. 17325-26-7, 0.163 g, 1.290 mmol) in.THF (10 mL) at 0 0C is added pMe2NPhP(Ph)2 (0.619 g, 1.925 mmol) and diisopropyl azodicarboxylate (94%, 0.414 g, 1.925 mmol). After 1 hour the mixture is warmed to room temperature and after 18 hours it is diluted with ethyl acetate and extracted with 1M aqueous HCI. The extracts are cooled to 0 0C, and the pH is adjusted to ca. 9 with ice-cold 4M aqueous NaOH. The basic aqueous phase is extracted three times with dichloromethane, and the combined organic phases are dried over magnesium sulfate, filtered through a cotton plug, and concentrated. The resulting residue is purified by silica gel flash chromatography (elution with dichloromethane- methanol, 1 :0 to 99:1 to 49:1) to afford 3-(5-fluoro-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; MS: (ESI) m/z 261.0 (M+H) The HCI salt of the title compound can be prepared by dissolution in diethyl ether followed by treatment with an excess of 1 N HCI in diethyl ether. The resulting heterogeneous solution is concentrated to furnish the HCI salt of 3-(5-fluoro-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester; 1H NMR (400 MHz1 CDCI3) delta ppm 2.06 – 2.20 (m, 1 H), 2.71 – 2.85 (m, 1 H), 2.87 – 3.00 (m, 1 H), 3.00 – 3.14 (m, 1 H), 3.87 (s, 3 H)1 6.47 (dd, J=7.7, 4.7 Hz, 1 H), 6.88 – 6.97 (m, 1 H), 7.01 (dd, J=8.6, 2.3 Hz1 1 H), 7.16 (dd, J=8.6, 5.1 Hz, 1 H), 7.19 (s, 1 H)1 7.77 (s, 1 H).
The synthetic route of 17325-26-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; NOVARTIS AG; WO2008/76336; (2008); A2;,
Imidazole – Wikipedia,
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