Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 21905451 | HCID 21905451 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 21905279 | HCID 21905279 | 70.1% |
Reaction Steps
To a solution of (RS)-2-(4-bromo-2,6-difluoro-phenyl)-N-(4-cyano-benzyl)-2-methoxy-acetamide (example 69.1, 247 mg) in 1,2-dimethoxyethane (5 ml) was added tetrakis(triphenylphosphine) palladium (0) (73 mg). A solution of phenylboronic acid (118 mg) in EtOH (2.1 ml) and a solution of sodium carbonate (563 mg) in water (3 ml) were added. The mixture was stirred for 1.5 h at 85° C. The solids were filtered off and the filtrate was evaporated. The product was purified by flash chromatography (cyclohexane/EtOAc 2:1=>EtOAc) to give (RS)-N-(4-cyano-benzyl)-2-(3,5-difluoro-biphenyl-4-yl)-2-methoxy-acetamide (172 mg). Off-white solid. MS 393.1 ([M+H]+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07129238B2 |
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| Source dataset | uspto-grants-2006_10 |
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| ORD ID | ord-ec93b54ad07544479477d951a0521ae3 |
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| Source note | uspto-grants-2006_10 |
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