In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 622392-04-5 as follows. Safety of 2-Bromo-5-iodopyrazine
Preparation 11 : iert-Butyl (2S)-2-[5-(5-bromopyrazin-2-yl)-1 H-benzimidazol-2-yl]pyrrolidine-1 – carboxylateTo ieri-butyl (2S)-2-[5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-benzimidazol-2-yl]pyrrolidine-1- carboxylate obtained from Preparation 6 (500 mg, 1.21 mmol) and 2-bromo-5-iodopyrazine obtained from Preparation 10 (310 mg, 1 .10 mmol) in toluene (12.5 ml_) and ethanol (1.6 ml_), were added [1 ,1- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (50 mg, 55 muiotaetaomicronIota) and sodium carbonate (1.1 ml_, 1 M aqueous solution, 1.1 mmol). The reaction mixture was heated at 60 C for 16 hours. After this time, the resulting mixture was cooled to room temperature, diluted with ethyl acetate (30 ml_) and washed with water. The aqueous layer was extracted again with ethyl acetate. The combined organic extracts were dried over MgS04 and the solvent was evaporated under reduced pressure. The crude product obtained was purified by flash chromatography (ethyl acetate : dichloromethane, 1 : 1 ) to give the title compound as a yellow solid (385 mg).LCMS (run time = 5 minutes, System D): Rt = 2.92 minutes; m/z 444 and 446 [MH+]H NMR (400 MHz, CD3OD): delta = 8.40-7.00 (br, 5H), 5.10-5.00 (m, 1 H), 3.75 (m, 1 H), 3.55 (m, 1 H), 2.55-2.35 (m, 1 H), 2.15-1.95 (m, 3H), 1 .10 (s, 9H).
According to the analysis of related databases, 622392-04-5, the application of this compound in the production field has become more and more popular.
Reference:
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; TRAN, Thien Duc; WAKENHUT, Florian; WO2011/154871; (2011); A1;,
Pyrazine – Wikipedia,
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