Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,1'-Biphenyl-4-yl-boronic acid | HCID 151253 | — |
| Reactant | HCID 86629498 | HCID 86629498 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57658004 | HCID 57658004 | 100.1% |
Reaction Steps
Purge with N2 a mixture of trifluoro-methanesulfonic acid 3,5-dichloro-4-[3-(4,4-difluoro-piperidin-1-yl)-2-oxo-pyrrolidin-1-ylmethyl]-phenyl ester (0.097 g, 0.19 mmol), 4-biphenylboronic acid (0.045 g, 0.23 mmol) in THF (5 mL), and 2M sodium carbonate (0.29 mL). Treat the reaction with Pd(PPh3)4 (0.011 g, 0.01 mmol) and heat to 80° C. for 1 hour under N2. Cool the reaction, dilute with ethyl acetate, and wash with water. Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford crude product. Purify on silica with 100% ethyl acetate to afford 0.098 g (100%) of the titled product. Rf=0.44 (100% ethyl acetate). MS (m/z): 515 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07994176B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-6c6403c2ff664ee88e854d073d2f9684 |
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| Source note | uspto-grants-2011_08 |
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