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| | 5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile Basic information |
| Product Name: | 5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile | | Synonyms: | 5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile;TAK-438( Vonoprazan fumarate) intermediate 2;Vonoprazan Fumarate impurity B;TAK438 Impurity 19;1H-Pyrrole-3-carbonitrile,5-(2-fluorophenyl)-;Vonoprazan impurity 32/5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile;Vonoprazan impurity SM2-I: 3-nitrile;Vonoprazan-4 | | CAS: | 1240948-77-9 | | MF: | C11H7FN2 | | MW: | 186.19 | | EINECS: | 809-912-0 | | Product Categories: | 1240948-77-9 | | Mol File: | 1240948-77-9.mol |  |
| | 5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile Chemical Properties |
| Boiling point | 364.7±32.0 °C(Predicted) | | density | 1.28±0.1 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | pka | 13.87±0.50(Predicted) | | form | Solid | | Appearance | Light yellow to brown Solid | | Dielectric constant | 5.5（22.0℃） | | InChI | InChI=1S/C11H7FN2/c12-10-4-2-1-3-9(10)11-5-8(6-13)7-14-11/h1-5,7,14H | | InChIKey | ZDEFHFJZEDEKJO-UHFFFAOYSA-N | | SMILES | N1C(C2=CC=CC=C2F)=CC(C#N)=C1 |
| | 5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile Usage And Synthesis |
| Description | 5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile is an important pharmaceutical intermediate component for the preparation of vonorasan fumarate, vonoprazan key intermediate, and vorexanol fumarate intermediate. | | Uses | 5-(2-Fluorophenyl)-1H-pyrrole-3-carbonitrile is an impurity of Vonoprazan (V767010) a novel potassium-competitive acid blocker for the treatment of acid-related diseases. | | Application | 5-(2-Fluorophenyl)-1H-pyrrole-3-carbonitrile is a crucial pharmaceutical intermediate primarily used as the key raw material for synthesizing Vonoprazan Fumarate (a novel potassium-competitive acid blocker for treating gastric ulcers, duodenal ulcers, reflux esophagitis, etc.).It can also serve as a building block for the development of pyrrole-containing drug compounds, and as a reference standard for impurity analysis and reaction monitoring in drug synthesis. | | Synthesis | To a 100 mL four-necked flask under nitrogen protection was added nickel ryenne (12.6 g), N,N-dimethylacetamide (30 mL), morpholine (1.36 mL, 15.6 mmol), and 2,2'-dithiobis[5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile] (4.50 g, 10.4 mmol) to a 15 mL solution of N,N-dimethylacetamide (15 mL) solution. The reaction mixture was heated at reflux at 105 °C for 5.5 hours. After completion of the reaction, the mixture was cooled, the catalyst was removed by filtration, and the filter cake was washed sequentially with N,N-dimethylacetamide and ethyl acetate. Liquid-liquid partitioning was carried out by adding 5% brine to the filtrate and washing solution. The aqueous layer was extracted three times with ethyl acetate. The organic layers were combined, washed with 5% brine and concentrated to dryness under reduced pressure. Ethanol (22.5 mL) was added to the residue and heated to dissolve. Water (45 mL) was added to induce crystallization. The slurry was heated to reflux for 1 hour, then cooled to room temperature and an ice-water mixture was added. Crystals were collected by filtration and washed with an ice-cooled water/ethanol (1:2, 10 mL) mixture. The crystals were dried under reduced pressure at 50 °C to afford the title compound 5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile (3.45 g, 85% yield). The product was confirmed by 1H-NMR (DMSO-d6, TMS, 300 MHz), mass spectrometry (EI) and elemental analysis. | | References | [1] Patent: US2011/306769, 2011, A1. Location in patent: Page/Page column 30-31 |
| | 5-(2-fluorophenyl)-1H-pyrrole-3-carbonitrile Preparation Products And Raw materials |
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