Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Furan-3-boronic acid | HCID 2734358 | — |
| Reactant | HCID 66680314 | HCID 66680314 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66680416 | HCID 66680416 | 59% |
Reaction Steps
210 mg (10.7 mmol) of 3-furan boronic acid, 500 mg (7.13 mmol) of methyl 2-{[(3-bromophenoxy)acetyl]amino}-5-chlorobenzoate, 144 mg (0.713 mmol) of tetrakis(triphenylphosphine)palladium(0), and 613 mg (10.7 mmol) of cesium carbonate were heated under reflux for 6 hours in THF (5 mL). After the completion of the reaction, ethyl acetate was added thereto, and the mixture was stirred for 1 hour and filtered using a silica gel pad. After the filtrate was condensed, the obtained crude product was separated and purified by silica gel column chromatography. IPE was added to the resulting solids, followed by collection by filtration, washing with IPE, and drying under reduced pressure at 50° C. for 5 hours, thereby giving 286 mg of methyl 5-chloro-2-({[3-(furan-3-yl)phenoxy]acetyl}amino)benzoate (yield: 59%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785473B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-bc1da41f4b08480b95dc39a9f8f3e850 |
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| Source note | uspto-grants-2014_07 |
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