Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Ethyl 4-bromobenzoate | HCID 22043 | — |
| Reactant | tert-Butyl carbazate | HCID 70091 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 59239861 | HCID 59239861 | 97.7% |
Reaction Steps
Ethyl 4-bromobenzoate (25.0 g), tert-butyl hydrazinecarboxylate (28.8 g), tris(dibenzylideneacetone)dipalladium(0) (1.00 g), 1,1′-bis(diphenylphosphino)ferrocene (1.82 g) and cesium carbonate (35.6 g) were added to toluene (220 ml) under an argon atmosphere, and the mixture was stirred at 100° C. for 18 hr. The reaction mixture was filtered through celite, and the residue was washed with dichloromethane. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1, volume ratio) to give the title compound (29.9 g). A part of the compound was recrystallized from ethyl acetate-diisopropyl ether to give a colorless crystal.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07989445B2 |
|---|
| Source dataset | uspto-grants-2011_08 |
|---|
| ORD ID | ord-4c9a1ae2387f44929b8b5561e0095333 |
|---|
| Source note | uspto-grants-2011_08 |
|---|