Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | Benzoic acid, 2-fluoro-, methyl ester | HCID 67854 | — |
| Edukt | HCID 58992652 | HCID 58992652 | — |
| Katalysator | Tetrabutylammonium Iodide | HCID 67553 | — |
| Lösungsmittel | Dimethyl Sulfoxide | HCID 679 | — |
| Produkt | HCID 58992615 | HCID 58992615 | 58% |
Reaktionsschritte
N-(Pyrrolidin-3-yl methyl)-2-(4-chlorophenyl)-4-methylthiazole-5-carboxamide (168 mg, 0.500 mmol) and methyl 2-fluorobenzoate (0.127 mL, 1.00 mmol) were dissolved in dimethylsulfoxide (4 mL). To this solution, potassium carbonate (138 mg, 1.00 mmol) and tetrabutylammonium iodide (18.5 mg, 0.0500 mmol) were added and the mixture was stirred at 140° C. for 6 hours. Subsequently, the reaction mixture was allowed to cool and water was added. The mixture was then extracted with ethyl acetate and the extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=4:1->2:1) gave 136 mg (58%) of the desired compound as a colorless amorphous product.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07902367B2 |
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| Quelldatensatz | uspto-grants-2011_03 |
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| ORD ID | ord-f569914275bf4e65bc69dfc738e7627e |
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| Quellennotiz | uspto-grants-2011_03 |
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