Synthetic Route of 10010-93-2,Some common heterocyclic compound, 10010-93-2, name is 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, molecular formula is C5H5F3N2, 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.
EXAMPLE 2. Preparation of N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-[(1R)-1-phenylpropyl]-4-thiazolecarboxamide (Compound 117) Step A: Preparation of 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-acetic acid. A mixture of 3-methyl-5-trifluoromethylpyrazole (10.0 g, 66.7 mmol), ethyl bromoacetate (11.1 mL, 100 mmol) and potassium carbonate (18.4 g, 133 mmol) in 80 mL of N,N-dimethylformamide was stirred at ambient temperature overnight. The orange mixture was filtered, diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated under reduced pressure to give 15.7 g of the pyrazole ester. The ester, in 100 mL of tetrahydrofuran, was treated with 11 mL of a 50 % aqueous NaOH solution in 90 mL of water and stirred at ambient temperature overnight. The tetrahydrofuran was removed under reduced pressure and the aqueous solution was washed with ether and acidified with conc. HCl to pH 1 to give a precipitate. The precipitate was filtered, washed with water and dried to give 12.1 g of the title compound as a white solid. 1H NMR (Acetone-d6) delta 2.35 (s, 3H), 5.07 (s, 2H), 6.45 (s, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, its application will become more common.
Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2007/14290; (2007); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics