HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1645280Generated: October 25, 2026
Water → Methyl 4-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)-3-fluorobenzoate
https://huagongshe.com/reaction/1645280
Participants
| Role | Name | HCID | Charge |
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| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Fluoro-4-(methoxycarbonyl)benzeneboronic acid | HCID 24824345 | — |
| Reactant | 3-((5-Bromofuran-2-yl)methylene)-5-chloroindolin-2-one | HCID 66772829 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | Methyl 4-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)-3-fluorobenzoate | HCID 66772791 | — |
Reaction Steps
To 3-((5-bromofuran-2-yl)methylene)-5-chloroindolin-2-one (150 mg, 0.466 mmol) in dioxane/water (2850/150 μL) was added 2-fluoro-4-(methoxycarbonyl)phenylboronic acid (111 mg, 0.559 mmol) and Cs2CO3 (456 mg, 1.398 mmol). The mixture was degassed with nitrogen for 5 minutes, then PdCl2 dppf (17 mg, 0.023 mmol) was added. The mixture was heated in microwave for 40 minutes at 110° C. Water was added and the solid formed was isolated by filtration to yield methyl 4-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)-3-fluorobenzoate. LCMS (M+1=398).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08124649B2 |
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| Source dataset | uspto-grants-2012_02 |
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| ORD ID | ord-b955915415f340128430572236e447bc |
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| Source note | uspto-grants-2012_02 |
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