Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-(Trifluoromethyl)benzeneboronic acid | HCID 2734387 | — |
| Reactant | HCID 57849627 | HCID 57849627 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 57849496 | HCID 57849496 | — |
Reaction Steps
The above compound could be made in the following manner: 1 eq. of 4-(4-Bromo-benzyl)-2-isopropyl-morpholine could be combined with 1.5 eq. of 2-(Trifluoromethyl)phenyl boronic acid, 10 mol % of tetrakis(triphenylphosphine)palladium(0), 6.7 eq. of 2M sodium carbonate solution, toluene and ethanol. The reaction mixture could be heated in a sealed tube at 120° C. overnight in an oil bath. The reaction mixture is filtered through Celite and concentrated in vacuo. The residue could be diluted with water and extracted with ethyl acetate. The combined organic phases could be washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material could be purified by flash chromatography to afford product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07595397B2 |
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| Source dataset | uspto-grants-2009_09 |
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| ORD ID | ord-d5dde1b76a044244a8982256f1c7d63d |
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| Source note | uspto-grants-2009_09 |
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