Reference of 4522-35-4,Some common heterocyclic compound, 4522-35-4, name is 3-Iodo-1H-pyrazole, molecular formula is C3H3IN2, 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 C: 5-(3-Iodo-lH-pyrazol-l -yl)-3-(trifluoiOmethyl)pyridazine To 3-iodopyrazole (124 mg, 0.641 mmol) in DMF (2 mL)was added potassium tert- butoxide (53 mg, 0.472 mmol) at 0 C. The mixture was stirred at room temperature for 15 min. It was transfered into a solution of 5- chloro-3- (trifluoromethyl)pyridazine (78 mg, 0.427 mmol) in DMF (2 mL) at 0 C. It was wanned to room temperature, stirring for 30 min. It was diluted with EtOAc(20 mL), washed with water (3 x 20 mL), the combined aqueous layers were extracted with EtOAc (30 mL), the combined organic layers were washed with brine (30 mL), dried over Na2S04, filtered and concentrated. The residue was purified by flash chromatography (ISCO Combiflash, 12 g, 0-100% EtOAc in hexanes) to give a mixture of 3-iodopyrazole and the desired product (1 :2, 180 mg). It was disolved in anhydrous CH2C12 (2 mL) and added a little bit of DMAP and of di-fert-butyl dicarbonate (~ 100 mg). It was stirred at room temperature for 10 min and purified by flash chromatography (ISCO Combiflash, 0-40% EtOAc in hexanes) to give 5 -(3- iodo-lH-pyrazol-l-yl)-3-(trifluoromethyl)pyridazine, as white solid. LCMS calc. = 340.95, found = 340.84 (M+H)+. NMR (500 MHz, CHCl3-d): delta 9.78 (d, J= 2.5 Hz, 1 H); 8.17 (d, J= 2.5 Hz, 1 H); 8.04 (d, J= 2.7 Hz, 1 H); 6.84 (d, J = 2.7 Hz, 1 H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodo-1H-pyrazole, its application will become more common.
Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
Pyrazole – Wikipedia,
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