Application of 622392-04-5, These common heterocyclic compound, 622392-04-5, name is 2-Bromo-5-iodopyrazine, 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.
Preparation 67: iert-Butyl (2S)-2-{4-[4-(5-bromopyrazin-2-yl)phenyl]-1 H-imidazol-2-yl}pyrrolidine-1- carboxylateMethod A:Potassium phosphate (7.39 g, 34.81 mmol) was added to a stirred solution of 2-bromo-5-iodopyrazine obtained from Preparation 10 (7.65 g, 17.41 mmol) and tert-butyl (2S)-2-{4-[4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)phenyl]-1 H-imidazol-2-yl}pyrrolidine-1 -carboxylate obtained from Preparation 3 (6.45 g, 22.63 mmol) in a mixture of 1 ,4-dioxane : water (3:7, 500 mL). The mixture was degassed for 20 minutes after which time tetrakis(triphenylphosphine)palladium (0) (2.00 g, 1 .74 mmol) was added and the reaction heated to 90C for 2 hours. After this time, the reaction mixture was cooled to room temperature and poured into a saturated solution of sodium bicarbonate (500 mL). The product was extracted with ethyl acetate (3 x 500 mL). The combined organic layers were dried over sodium sulphate and the solvent was removed under reduced pressure to a brown crude oil. The crude product was purified by flash chromatography (ethyl acetate:dichloromethane, 50 : 50 to 100 : 0) to give the title compound as a pale yellow solid (5.56 g).LCMS: (run time = 4.5 minutes, System J): Rt = 2.22 minutes; m/z 470.19 and 472.07 [MH+]H NMR (400 MHz, CD3OD) delta = 8.95 (s, 1 H), 8.75 (s, 1 H), 8.1 (d, 2H), 7.85 (d, 2H), 7.50-7.40 (m, 1 H), 4.90- 4.80 (m, 1 H), 3.75-3.65 (m, 1 H), 3.55-3.45 (m, 1 H), 2.40-2.30 (br. m, 1 H), 2.10-1.90 (m, 3H), 1.25 (s, 9H)
The synthetic route of 622392-04-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; PFIZER LIMITED; MILBANK, Jared Bruce John; TRAN, Thien Duc; WAKENHUT, Florian; WO2011/154871; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem