Some common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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. Application In Synthesis of 2-(Difluoromethyl)-1H-benzo[d]imidazole
Example 55 1-(2-(2-(difluoromethyl)-1H-benzo[c]imidazol-1-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)ethanone To a 5 mL microwave vial equipped with a magnetic stir-bar were added 1-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)ethanone (300 mg, 1.116 mmol), 2-(difluoromethyl)-1H-benzo[d]imidazole (179 mg, 1.063 mmol), tris(dibenzylideneacetone)dipalladium(0) (38.9 mg, 0.043 mmol) and cesium carbonate (520 mg, 1.595 mmol). The vial was evacuated and filled with nitrogen four times and then sealed. DMF (2.1 mL) was added to give an orange suspension, which was heated to 140 C. for 45 minutes. The reaction mixture was heated for an additional 30 minutes, was subsequently diluted with ACN (3 mL), and was passed through a syringe filter. The filtrate was directly purified by preparatory HPLC using a gradient of 40-60% CH3CN (with 0.035% TFA) in H2O (with 0.05% TFA). Lyophilization of the collected fractions gave a TFA salt of the title compound (135 mg, 31.7%). ESI-MS m/z [M+H]+ calc’d for C19H18F2N6O2, 401.15. found 401.3.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 705-09-9, its application will become more common.
Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2012/220575; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem