Application of 401567-00-8,Some common heterocyclic compound, 401567-00-8, name is 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, molecular formula is C8H4ClN3, 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.
A mixture of 2-chloro-1H-benzimidazole~5-carbonitrile (3.0 g, 17 mmol, 1.0 eq), (2S)-2-[(4-tert-0 butylphenoxy)methyl]oxirane (1-2) (3.5 g, 19 mmol, 1.1 eq) and cesium carbonate (0.10 g, 0,31 mmol, 0.020 eq) were heated under microwave irradiation at 130 C for 45 minutes. Ethyl acetate was added (200 ml) and the organic layer was washed with water (50 ml) and dried over sodium sulfate. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) followed by purification by super critical fluid chromatography (ChiraiPak AS-5 H, 21x250mm, 90/10 CO2/Methanol, 70 ml/min) to separate regioisomers and yield (2S)-2- ( { [tert-butyl(dimethyl )si Iy I ]oxy } methy l)-2 , 3 -dihydro [1,3] oxazolo [3 ,2 -a] benzi midazole-7 – carbonitrile (1-3) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.80 (s, 1H), 7.42 (d, 1H, J = 8.2 Hz), 7.19 (d, 1H, J = 8.2 Hz), 5.51-5.44 (m, 1H), 4.35-4.26 (m, 2H), 4.10 (dd, 1H, J – 1 1.8, 3.8 Hz), 3.95 (d, 1H, J – 3.1 Hz), 0.76 (s, 9 H), 0.00 (s, 6 H). LRMS m/z (M+H) 330.0 found,0 330.2 required. The alternative regioisomer (1-4) was also isolated and characterized.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-1H-benzo[d]imidazole-5-carbonitrile, its application will become more common.
Reference:
Patent; MERCK & CO., INC.; WO2009/140163; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem