Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | HCID 90449646 | HCID 90449646 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 90449870 | HCID 90449870 | 58.2% |
Reaction Steps
1-(1′-Acetyl-5-hydroxyspiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (40 mg, 0.122 mmol) was dissolved in methylene chloride (1.5 mL). Thereafter, 4-fluorophenylboronic acid (34 mg, 0.244 mmol), copper(II) acetate (22 mg, 0.122 mmol), triethylamine (62 mg, 0.610 mmol), and molecular sieves 4A (40 mg) were added to the above obtained solution, and the thus obtained mixture was then stirred at room temperature for 18 hours. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then purified by silica gel column chromatography (ethyl acetate) to obtain 1-(1′-acetyl-5-(4-fluorophenoxy)spiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (30 mg, 56%) in the form of a light yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08921576B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-60bb67b61a3c4a90b9187d9a0e028678 |
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| Source note | uspto-grants-2014_12 |
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