Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 5233012 | — |
| Reactant | HCID 67071846 | HCID 67071846 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 67071912 | HCID 67071912 | 6% |
Reaction Steps
A suspension of 2-aminocarbonylamino-5-bromo-6-methoxyindole-3-carboxamide (Compound No.7-1, 86 mg, 0.26 mmol), vinylboronic acid pinacol ester (121 μL, 0.40 mmol), tetrakis(triphenylphosphine)palladium(0) (32 mg, 0.027 mmol) and sodium hydrogen carbonate (56 mg, 0.66 mmol) in 1,4-dioxane-water solution (3:1, 15 mL) was stirred overnight at 110° C. under argon atmosphere. After cooling, ethyl acetate (20 mL) and brine (15 mL) were added and separated. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (4 mg) as a dark green solid (6%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08445529B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-c69cae591dea412999da5e59c321f5d5 |
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| Source note | uspto-grants-2013_05 |
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