Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Reactant | HCID 67111227 | HCID 67111227 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67237886 | HCID 67237886 | 78.1% |
Reaction Steps
To a suspension of 5-bromo-thiophene-2-carboxylic acid 3,5-difluoro-4-methanesulfonylamino-benzylamide (100 mg, 0.235 mmol), Pd(PPh3)4 (4.1 mg, 0.0035 mmol), and 4-trifluoromethyl phenyl boronic acid (53.5 mg, 0.282 mmol) in toluene (1 mL) was added 2N—Na2CO3 (0.5 mL)/EtOH (0.5 mL). The mixture was stirred 3 hours at 110° C. and was diluted with EtOAc. The mixture was washed with 1N HCl, water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane) to give title compound (90 mg, 78%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08691855B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-1e5707ca51e846eaae92680296436f02 |
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| Source note | uspto-grants-2014_04 |
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