Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Reactant | Chloroform water | HCID 22418719 | — |
| Reactant | HCID 87717666 | HCID 87717666 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 85972743 | HCID 85972743 | 34.3% |
Reaction Steps
To a mixture of Example 30 (0.08 g, 0.2 mmol) and 4-trifluoromethylphenylboronic acid (0.057 g, 0.3 mmol) in anhydrous dioxane (2 ml) was added (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (0.007 g, 0.009 mmol) and saturated aqueous sodium carbonate solution (0.3 ml). The mixture was irradiated in a microwave reactor at 170° C. for 10 minutes, allowed to cool to room temperature and poured onto a mixture of chloroform/water (30 ml/10 ml). The phases were separated and the aqueous phase was extracted two times more with chloroform. The combined organic layers were washed with brine, dried over sodium sulfate and adsorbed onto silica gel. Purification by flash column chromatography (ethyl acetate) yielded the title compound (35 mg, 34%) as a yellow solid. m/z (ES+) 511 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07442701B2 |
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| Source dataset | uspto-grants-2008_10 |
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| ORD ID | ord-18b80516004a4db1bcb6cb053a92b4af |
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| Source note | uspto-grants-2008_10 |
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