Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | HCID 2734648 | — |
| Reactant | HCID 31775116 | HCID 31775116 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 131729798 | HCID 131729798 | 83.4% |
Reaction Steps
To a suspension of tert-butyl {(1S)-1-benzyl-2-[(4-bromophenyl)amino]-2-oxoethyl}carbamate (1.0 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (587 mg) and potassium phosphate (1.52 g) in dimethoxyethane (30 mL) was added 1,1′-bis(diphenylphosphino)ferrocene palladium(II) chloride (58 mg) and the mixture was stirred at 120° C. for 4 hours. Water was added and the mixture was extracted with chloroform. The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to afford tert-butyl[(1S)-1-benzyl-2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl]carbamate (830 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08211919B2 |
|---|
| Source dataset | uspto-grants-2012_07 |
|---|
| ORD ID | ord-4670aaeac54247f6a07dd80b87a4f2f2 |
|---|
| Source note | uspto-grants-2012_07 |
|---|
