Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | HCID 86630018 | HCID 86630018 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86630017 | HCID 86630017 | 17.3% |
Reaction Steps
Bring a mixture of trifluoro-methanesulfonic acid (R)-3,5-dichloro-4-[1-(4-hydroxy-piperidin-1-yl)-2-oxo-pyrrolidin-3-ylmethyl]-phenyl ester (0.102 g, 0.21 mmol), 4-fluorophenylboronic acid (0.035 g, 0.25 mmol), sodium carbonate (0.066 g, 0.62 mmol) in THF (10 mL) and water (3 mL) to 60° C. To the mixture at 60° C., add Pd(PPh3)4 (0.015 g, 0.011 mmol), raise the reaction temperature to 80° C., and stir for 2.5 hours. Cool the reaction, dilute with ethyl acetate, and wash with water and brine. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify on silica gel column and HPLC (Reverse Phase) to afford 0.02 g of the titled product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08153807B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-fe7be5c3b4b14aa48bddef315c53e159 |
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| Source note | uspto-grants-2012_04 |
|---|