Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3,4-Difluorobenzeneboronic acid | HCID 2734337 | — |
| Reactant | HCID 90101239 | HCID 90101239 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 73775733 | HCID 73775733 | 53.2% |
Reaction Steps
15.0 mg (0.03 mmol) of 5-chloro-4-((6-chloro-4-(1H-pyrazol-4-yl)pyridin-3-yl)oxy)-2-fluoro-N-(thiazol-4-yl)benzenesulfonamide was dissolved in 1.5 mL of 1,4-dioxane, and 7.1 mg (0.05 mmol) of (3,4-difluorophenyl)boronic acid was added thereto, and then 3.5 mg (10 mol %) of Pd(PPh3)4, 12.4 mg (0.09 mmol) of K2CO3, and 0.3 mL of H2O were added thereto. After reacting with microwave reactor at 150° C. for 30 minutes, the solvent was removed, and the remaining material was diluted with ethyl acetate and the organic layer was separated, and washed with saturated sodium chloride. The organic layer was collected, dried with magnesium sulfate to remove water, and concentrated under reduced pressure, and the residue was purified by column chromatography (developing solvent, dimethylchloride:methanol=20:1) to obtain 9.0 mg (31.9% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09376429B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-17611c925cc3427caac3ad26b3df0cd9 |
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| Source note | uspto-grants-2016_06 |
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