Application of 5604-46-6 ,Some common heterocyclic compound, 5604-46-6, molecular formula is C5H3Cl2N3O, 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.
The appropriately substituted benzyl triphenylphosphonium halide (e.g., 4- chlorobenzyltriphenylphosphonium chloride, 0.66 g, 1.56 mmol), was suspended in anhydrous THF (5.0 mL) with stirring under argon and cooled to -78 0C. Then, nBuLi (0.6 mL, 2.5 M in hexane) was added dropwise over 20 minutes and stirring was continued for an additional 0.5 h. Compound 1 (0.2 g, 1.04 mmol) was suspended/partially dissolved in anhydrous THF (15.0 mL) and added dropwise to the ylide solution. The cooling bath was removed and the mixture was stirred at room temperature for 2 h whereby TLC (1 :20 THF- CH2Cl2) showed no remaining starting material, 1. The yellow solution was cooled to -78 0C and treated cautiously with ammonium chloride (satd, 15 mL). The mixture removed from the cooling bath, and stirring was continued for 1.5 h before EtOAc ( 10.0 mL) was added. The organic phase was separated, washed with water (1 x 10 mL), dried (Na2SO4), filtered, and concentrated to dryness. Flash chromatography (1 :20 THF-CH2CI2) provided compound 2a (0.1 18 g, 37.7%, mixture of cis and trans isomers) as an off-white solid.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5604-46-6, its application will become more common.
Reference:
Patent; SCHERING CORPORATION; SOUTHERN RESEARCH INSTITUTE; NJOROGE, F. George; PIWINSKI, John J.; SHIH, Neng-Yang; KWONG, Cecil D.; ANANTHAN, Subramaniam; CLARK, Jeremy; GENG, Feng; KEZAR, III, Hollis S.; MADDRY, Joseph A.; REYNOLDS, Robert C.; ROYCHOWDHURY, Abhijit; SECRIST, III, John A.; WO2010/22128; (2010); A1;,
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