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| | Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate Basic information |
| Product Name: | Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate | | Synonyms: | 2,4-DIMETHYL-1H-PYRROLE-3-CARBOXYLIC ACID ETHYL ESTER;ETHYL 2,4-DIMETHYL-1H-PYRROLE-3-CARBOXYLATE;ETHYL 2,4-DIMETHYL-PYRROLE-3-CARBOXYLATE;ETHYL 2,4-DIMETHYLPYRROLE-3-CARBOXYLIC ACID;1H-Pyrrole-3-carboxylic acid, 2,4-dimethyl-, ethyl ester;Ethyl 2,4-dimethylpyrrole-3-carboxylate 98%;Pyrrole-3-carboxylic acid, 2,4-dimethyl-, ethyl ester;2,4-Dimethyl-1H-pyrrole-3-carboxylic acid ethyl | | CAS: | 2199-51-1 | | MF: | C9H13NO2 | | MW: | 167.21 | | EINECS: | 606-885-5 | | Product Categories: | Sunitinib Intermediate;Intermediate of sunitinib malate;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Pharmaceutial intermediates;2199-51-1 | | Mol File: | 2199-51-1.mol |  |
| | Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate Chemical Properties |
| Melting point | 122-123°C | | Boiling point | 162°C/11mmHg(lit.) | | density | 1.1222 (rough estimate) | | refractive index | 1.4680 (estimate) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | DMSO (Soluble), Chloroform (Slightly), Methanol (Slightly) | | pka | 16.44±0.50(Predicted) | | form | Solid | | color | Red to Very Dark Red | | λmax | 258nm(EtOH)(lit.) | | InChI | InChI=1S/C9H13NO2/c1-4-12-9(11)8-6(2)5-10-7(8)3/h5,10H,4H2,1-3H3 | | InChIKey | QWSFDUPEOPMXCV-UHFFFAOYSA-N | | SMILES | N1C=C(C)C(C(OCC)=O)=C1C | | CAS DataBase Reference | 2199-51-1(CAS DataBase Reference) | | NIST Chemistry Reference | 2,4-Dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester(2199-51-1) |
| | Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate Usage And Synthesis |
| Chemical Properties | White to light brown crystalline | | Uses | ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate is used in the preparation of blue pyrrole dyes. It is also used as an intermediate in the synt hesis of receptor tyrosine kinase (RTK) inhibitors and their metabolites. | | Uses | 2,4-Dimethyl-1H-pyrrole-3-carboxylic Acid Ethyl Ester is used in the preparation of blue pyrrole dyes. 2,4-Dimethyl-1H-pyrrole-3-carboxylic Acid Ethyl Ester is also used as an intermediate in the synthesis of receptor tyrosine kinase (RTK) inhibitors and their metabolites. | | Synthesis | Step (ii): Preparation of 2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester
In a 10-liter four-necked round-bottomed flask equipped with a mechanical stirrer, thermometer casing, gas introduction tube, and air condenser, 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester (II) (1.5 kg, 5.6 mol) and isopropanol (4.5 L) were added and stirred at 25-30 °C. Concentrated hydrochloric acid (2.2 L) was added slowly through the addition funnel. After addition, the reaction mixture was warmed up to 45-50 °C and maintained at this temperature until complete cessation of gas release. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the solution was cooled to 25-30 °C and quenched in an ice-water bath. The product was separated by filtration and dried at 50 °C. A dried product of 721.3 g was obtained with 77.3% yield and >96% HPLC purity. | | References | [1] Synlett, 2010, # 17, p. 2561 - 2564
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3062 - 3065
[3] Journal of the American Chemical Society,
[4] Journal of the American Chemical Society, 2009, vol. 131, p. 8578 - 8586
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 139 - 146 |
| | Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate Preparation Products And Raw materials |
| Raw materials | 1H-Pyrrole-1,3-dicarboxylic acid, 2,4-dimethyl-, 1-(1,1-dimethylethyl) 3-ethyl ester-->2-BENZYL 4-ETHYL 3,5-DIMETHYL-1H-PYRROLE-2,4-DICARBOXYLATE-->ETHYL 3-METHYL-4-OXOCROTONATE-->4-(Ethoxycarbonyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid-->3,5-Dimethylpyrrole-2,4-dicarboxylic acid 2-t-butyl ester-4-ethyl ester-->Diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate-->Methyllithium-->Ethyl acetoacetate-->Acetonitrile-->Hydrochloric acid | | Preparation Products | (Z)-ethyl 5-((5-fluoro-2-oxoindolin-3-ylidene)Methyl)-2,4-diMethyl-1H-pyrrole-3-carboxylate-->ETHYL 2,4-DIMETHYL-5-NITRO-1H-PYRROLE-3-CARBOXYLATE-->1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-5-(1-oxopropyl)-,ethylester(9CI)-->Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate |
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