Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Carbonate Ion | HCID 19660 | — |
| Reactant | 3-Formylphenylboronic acid | HCID 2734356 | — |
| Reactant | 5-bromo-3-(1-{[2-(methyloxy)ethyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide | HCID 59600662 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59003285 | HCID 59003285 | 48.4% |
Reaction Steps
To a solution of 5-bromo-3-(1-{[2-(methyloxy)ethyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (100 mg, 0.22 mmol) in dioxane (3.0 mL) and water (1.0 ml), (3-formylphenyl)boronic acid (186 mg, 1.25 mmol), Pd(PPh3)4 (25.0 mg, 10%) and cessium carbonate (200 mg, 0.45 mmol) were added. The reaction mixture was heated in a Smith synthesizer microwave at 160° C. for 20 min. All solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (ethyl acetate/hexane, 1/1) to yield the desired product (50.0 mg, 48%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07858796B2 |
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| Source dataset | uspto-grants-2010_12 |
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| ORD ID | ord-74b1384068a543808ad9abfd4056afd7 |
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| Source note | uspto-grants-2010_12 |
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