Electric Literature of 3398-16-1, A common heterocyclic compound, 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, molecular formula is C5H7BrN2, 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.
Step 6: 4-[3-(Cyanomethyl)-3-(3 ?,5 ?-dimethyl-lH, 1 ?11-4,4 ?-bipyrazol-l-yl)azetidin-lylJ-2, 5-difluoro-N-[(1S)-2, 2, 2-trifluoro-1-methylethylJbenzamideA mixture of 4- { 3 -(cyanomethyl)-3 – [4-(4,4,5 ,5 -tetramethyl- 1,3,2- dioxaborolan-2-yl)- 1H-pyrazol- 1 -yl]azetidin- l-yl} -2,5 -difluoro-N-[( 1 S)-2,2,2- trifluoro- 1 -methylethyl]benzamide (329 mg, 0.610 mmol), 4-bromo-3 ,5-dimethyl-pyrazole (206 mg, 1.18 mmol), tetrakis(triphenylphosphine)palladium(0) (110 mg,0.098 mmol) and sodium carbonate (320 mg, 3.0 mmol) in 1,4-dioxane (10 mL)/water(5 mL) was purged with nitrogen and stirred at 110 °C for 1 h. The reaction mixturewas diluted with EtOAc, washed with water and brine, concentrated. The residuewas purified first with silica gel (eluting with 0-100percent EtOAc/hexanes followed by10percent methanol/dichloromethane), and then by prep-LCMS (XBridge C18 column,eluting with a gradient of acetonitrile/water containing 0.1percent ammonium hydroxide,flow rate of 60 mL/min) to give the desired product (30 mg, 9.7percent). ?H NMR (500 MHz, DMSO-d6) oe 12.17 (1H, s), 8.45 (1H, d, J= 8.0 Hz), 8.10 (1H, s), 7.70 (1H,7.34 (1H, m), 6.61 (1H, s), 4.77 (1H, m), 4.62 (2H, d, J= 9.0 Hz), 4.39 (1H, d, J=Hz), 3.64 (2H, s), 2.22 (6H, s), 1.31 (6H, d, J= 7.0 Hz) ppm. LCMS calculated for C23H23F5N7Q (M+H): m/z = 508.2; Found: 508.0.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.