Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | HCID 178458419 | HCID 178458419 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178458423 | HCID 178458423 | 35.5% |
Reaction Steps
An amount of (4Z)-6-bromo-4-{[(3-hydroxy-4-propoxybenzyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione (0.15 g, 0.35 mmol) in 2 mL of N,N′-dimethylformamide is added to 4-fluorophenylboronic acid (0.073 g, 0.52 mmol), 0.02 g (0.03 mmol) of tetrakis(triphenylphosphine)-palladium(0) and 0.4 mL of saturated sodium carbonate solution. The reaction mixture is stirred at 100° C. under N2 for 2 h. Mass spectroscopy suggested the completion of the reaction. Solids were removed by filtration, and solvent is subsequently evaporated under high-pressure vacuum to brown solid. The residue is purified by HPLC to give 0.055 g (35.5% yield) of light brown solid: mp 194-195° C.; MS (ESI) m/z 445.2 (M+H)−1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07713994B2 |
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| Source dataset | uspto-grants-2010_05 |
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| ORD ID | ord-8ea119c1c88e4bd3a13c417575e2327e |
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| Source note | uspto-grants-2010_05 |
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