Application of 3398-16-1, The chemical industry reduces the impact on the environment during synthesis 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, I believe this compound will play a more active role in future production and life.
A mixture of 5-{3-(cyanomethyl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-isopropylpyrazine-2-carboxamide (256 mg, 0.567 mmol, from Example 2, step 2), 4-bromo-3,5-dimethyl-1H-pyrazole (119 mg, 0.681 mmol), dicyclohexyl(2?,4?,6?-triisopropylbiphenyl-2-yl)phosphine-(2?-aminobiphenyl-2-yl)(chloro)palladium (1:1) (67 mg, 0.085 mmol) and cesium carbonate (550 mg, 1.7 mmol) in 1,4-dioxane (2 mL)/ water (1 mL) was purged with nitrogen three times. The reaction was heated to 53¡ã C. for 2 h. The mixture was diluted with EtOAc, washed with brine, concentrated. The resulting reside was purified first on silica gel (eluting with 0-100percent EtOAc/hexanes followed by 10percent methanol/ dichloromethane), and then by prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1percent ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (0.1 g, 40percent). 1H NMR (500 MHz, DMSO-d6) delta 8.64 (1H, d, J=1.5 Hz), 8.12 (1H, s), 8.06 (1H, d, J=8.0 Hz), 7.96 (1H, d, J=1.0 Hz), 7.71 (1H, s), 4.72 (2H, d, J=9.5 Hz), 4.49 (1H, d, J=9.5 Hz), 4.08 (1H, m), 3.68 (2H, s), 2.22 (6H, s), 1.16 (6H, d, J=6.5 Hz) ppm. LCMS calculated for C21H26N9O (M+H)+: m/z=420.2. Found: 420.0.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-3,5-dimethylpyrazole, other downstream synthetic routes, hurry up and to see.