Some common heterocyclic compound, 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole, molecular formula is C10H9ClN2, 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. Product Details of 143426-52-2
Methyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylate (74 mg, 0.25 mmol, 1.0 eq.), cesium carbonate (240 mg, 0.74 mmol, 3.0 eq.), 1-(4-(chloromethyl)phenyl)-1H-pyrazole (71 mg, 0.37 mmol, 1.5 eq.) and Pd(dppf)Cl2.DCM (27 mg, 0.037 mmol, 0.15 eq.) were combined in a vial which was sealed and placed under an inert atmosphere. A 1,4-dioxane/H2O solution (5:1 v/v, 2 mL, degassed) was then added via syringe. The resulting mixture was heated to 90 C. for 1 h, after which time the reaction was cooled to r.t. and filtered through a plug of Celite with EtOAc and DCM. The product was observed to crash out upon Celite filtration, and the Celite pad was subsequently washed with a solution of 3:1 DCM/MeOH (with 1% AcOH). The resulting filtrate was concentrated under reduced pressure to give the title compound as a tan solid (78 mg, 100%), which was used directly without further purification. ES-MS [M+H]+=320.2.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 143426-52-2, its application will become more common.
Reference:
Patent; Vanderbilt University; Lindsley, Craig W.; Conn, P. Jeffrey; Engers, Darren W.; Engers, Julie L.; Long, Madeline; Bender, Aaron M.; US2020/131180; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics