Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 49803415 | HCID 49803415 | — |
| Catalyst | HCID 178420554 | HCID 178420554 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 49803416 | HCID 49803416 | 92.9% |
Reaction Steps
N-(2-aminophenyl)-4-((4-bromo-5,6-dimethoxy-1-oxoisoindolin-2-yl)methyl)benzamide (60 mg, 0.12 mmol) in Example 1, phenyl boronic acid (22 mg, 0.18 mmol, 1.5 equiv.), tetrakis(triphenyl-phosphino)palladium (8.4 mg, 0.0073 mmol, 6 mol %) and sodium carbonate (38 mg, 0.36 mmol, 3 equiv.) were dissolved in a mixture of dioxane and the distilled water (mixture ratio=4:1 (v/v), 5.0 mL) and the resulting solution was reacted at 150° C. under microwave for 15 mins. The resulting material thus obtained was diluted with ethyl acetate (EtOAc), dried over anhydrous MgSO4, and filtered with Celite. The filtrates were distilled under a reduced pressure to remove the solvent and the resulting residue was subjected to a silica gel column chromatography (EtOAc) to obtain the title compound (55 mg, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08716326B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-66f0c7349f9745b4ba79247b8841e527 |
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| Source note | uspto-grants-2014_05 |
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