Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 57634648 | HCID 57634648 | — |
| Catalyst | HCID 178418851 | HCID 178418851 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 54721906 | HCID 54721906 | — |
Reaction Steps
A solution of 8,9-dihydroxy-2-(3-iodobenzyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione (0.05 g, 0.121 mmol) in DMF (5 mL) was degassed for 5 minutes with nitrogen and placed under an atmosphere of nitrogen. To this was added phenyl boronic acid (0.015 g, 0.123 mmol), triethylamine (0.051 mL, 0.364 mmol), and bis(tri-t-butylphosphine)palladium(0) (0.003 g, 0,006 mmol) and heated with stirring at 110° C. overnight. The product mixture was concentrated under vacuum, and the residue was triturated with methylene chloride. The resultant precipitate was filtered off and the filtrate concentrated under vacuum. The filtrate residue was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Desired fractions were concentrated under vacuum to afford the title compound as off white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07517532B2 |
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| Source dataset | uspto-grants-2009_04 |
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| ORD ID | ord-7c4e5e086b864dc7ae310a528420cf4b |
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| Source note | uspto-grants-2009_04 |
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