52548-14-8, These common heterocyclic compound, 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, 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 2-iodo-5-methylbenzoic acid (1.5 g, 5.72 mmol), copper(I) iodide (1.090 g, 5.72 mmol) and (lR,2R)-N,N’-dimethyl-l,2-cyclohexanediamine (0.814 g, 5.72 mmol) was added DMF (10 ml) under nitrogen and then 2H-l,2,3-triazole (0.474 g, 6.87 mmol). The reaction mixture was heated at 120 C at the microwave Personal Chemistry for 15 minutes. UPLC- MS monitor showed that the reaction was complete. After cooling at room temperature water was added and the aqueous washed with EtOAc. Then the aqueous acidified to pH =1 with aqueous 1 M HC1 and extracted with EtOAc. The phases were separated on a hydrophobic frit, the combined organic solvent was removed to give the crude product (2.4 g).The crude compound was purified by silica gel chromatography (SNAP KP-Sil lOOg cartridge) eluted with 5 CV of a mobile phase prepared with DCM (959.04 ml), acetic acid (0.96 ml) and MeOH (40 ml). The evaporation of proper fractions gave a yellow oil which was triturated with toluene (4 x 50 ml) and the title compound D44 was obtained as yellow solid (540 mg).UPLC (Basic GEN QC): rt = 0.35 minutes, peak observed: 204 (M+l) Ci0H9N3O2 requires: 203.1H NMR (400 MHz, DMSO-d6) delta ppm 2.44 (s, 3 H) 7.52 (dd, 1 H) 7.59 (s, 1 H) 7.64 (d, 1 H) 8.06 (s, 2 H).
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 52548-14-8.
Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89606; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com