Category: 4522-35-4

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.

To a solution of 5-iodo-lH-pyrazole (0.2 g, 1.03 mmol) in dimethyl acetamide (3 ml) at 0C under argon was added sodium hydride 60% dispersion in mineral oil (41.2 mg, 1.03 mmol) in one portion. After stirring at 0C for 15 min, l-(bromomethyl)-4-methoxybenzene (207 mg, 1.03 mmol) was added in one portion. The cooling bath was removed and the mixture was stirred at room temperature for 17 hours. The mixture was diluted with ethyl acetate, and washed with water. The aqueous phase was back extracted with ethyl acetate. The combined organics were washed with water, dried over MgS04, filtered and evaporated. The residue was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethyl acetate (0 to 50 %) to provide the title compound as a colorless viscous oil (270 mg, 83 %). MS (m/e): 315.1 (M+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.

A common heterocyclic compound, 4522-35-4, name is 3-Iodo-1H-pyrazole, molecular formula is C3H3IN2, 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. 4522-35-4.

l-(But-3-en-l-yl)-3-iodo-lH-pyrazole. To a solution of 5-iodo-lH-pyrazole (1.34 g, 6.91 mmol, 1 equiv) in DMF (23 mL) was added 60% NaH (0.33 g, 8.29 mmol, 1.2 equiv). After 10 min, 4-bromobut-l-ene (0.84 mL, 8.29 mmol, 1.2 equiv) was added. After stirring 3 d, the reaction was added to water and extracted with EtOAc (x3). The combined EtOAc extracts were dried (Na2S04) and concentrated in vacuo. The crude product was purified by flash column chromatography (0-100%) EtOAc in hexane) to provide a 3: 1 mixture of product isomers (1.12 g, 65%>) as a colorless oil. Major isomer: 1H NMR (400 MHz, CDC13) delta 7.21 (d, J= 2.3 Hz, 1H), 6.39 (d, J= 2.3 Hz, 1H), 5.80 – 5.68 (m, 1H), 5.13 – 5.05 (m, 2H), 4.20 (t, J= 7.2 Hz, 2H), 2.61 (qt, J= 7.0, 1.3 Hz, 2H). Minor isomer: 1H NMR (400 MHz, CDC13) 7.53 (d, J= 1.8 Hz, 1H), 6.42 (d, J= 1.8 Hz, 1H), 5.81 (ddt, J= 17.1, 10.2, 6.9 Hz, 1H), 5.14 – 5.05 (m, 2H), 4.27 (t, J= 7.3 Hz, 2H), 2.65 – 2.58 (m, 2H).

The synthetic route of 3-Iodo-1H-pyrazole has been constantly updated, and we look forward to future research findings.