Application of 39806-90-1,Some common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, molecular formula is C4H5IN2, 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.
To a solution of l-methyl-4-iodo- lH-pyrazole (3 g, 14.42 mmol) in THF (40 mL) was added isopropylmagnesium chloride (2.0M in THF, 8.00 mL, 16.01 mmol) at O 0C. The mixture was stirred at O 0C for 1 h, cooled to -78 0C and JV-methoxy-Lambda’-methyl-2- ethoxyacetamide (product of Step A, 3.18 g, 21.63 mmol) was added. The mixture was slowly warmed to rt over 1.5 h. The reaction was cooled to -78 0C and quenched by the dropwise addition of saturated aqueous NH4CI. The reaction was warmed to rt and stored in the cold overnight. The reaction was then diluted with cold IN HCl, extracted four times with EtOAc, and the combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography eluting with a gradient of 50% EtOAc/hexanes to 100% EtOAc afforded 2-ethoxy-l-(l-methyl-pyrazol-4-yl)-ethanone. 1H NMR (500 MHz, CDCl3): 6 8.07(s, IH), 8.03 (s, IH), 4.38 (s, 2H), 3.96 (s, 3H), 3.62 (q, 2H), 1.29 (t, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-1-methyl-1H-pyrazole, its application will become more common.
Reference:
Patent; MERCK SHARP & DOHME CORP.; GUO, Liangqin; LIU, Jian; NARGUND, Ravi, P.; PASTERNAK, Alexander; YANG, Lihu; YE, Zhixiong; WO2010/51177; (2010); A1;,
Pyrazole – Wikipedia,
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