Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Fluoroethyl bromide | HCID 12982 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 57520095 | HCID 57520095 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 57520172 | HCID 57520172 | 30% |
Reaction Steps
The reaction mixture containing 0.27 g of 1-(6-(piperidin-4-yl)quinolin-4-yl)-3-(6-(trifluoromethyl)pyridin-2-yl)urea (0.650 mmol), 0.073 ml of 1-bromo-2-fluoroethane (0.975 mmol), 1.059 g of cesium carbonate (3.25 mmol) and 6.5 of dioxane was shaken in a flask at 60° C. for 4 h. Due to non complete reaction, additional 0.049 ml of 1-bromo-2-fluoroethane (0.650 mmol) were added and the reaction mixture was shaken at 60° C. for 18 h. Saturated sodium bicarbonate solution was added and the mixture extracted three times with ethyl acetate. The combined organic phases were washed once with brine, dried over sodiumsulfat and the solvent removed under reduced pressure. After purifying of the raw material (190 mg) by column chromatography (silica gel, DCM/MeOH 95:5) 90 mg of the desired product were obtained as beige powder (yield: 30%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09090592B2 |
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| Source dataset | uspto-grants-2015_07 |
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| ORD ID | ord-e719c958e65140f394d236df1ff38a7e |
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| Source note | uspto-grants-2015_07 |
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