HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 2-{4-[2-(3,4-Dimethyl-phenyl)-ethyl]phenylamino)-5-nitrobenzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl 2-Bromo-5-nitrobenzoate | HCID 245494 | — |
| Reactant | 4-[2-(3,4-Dimethylphenyl)ethyl]-benzenamine | HCID 14555209 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Di-p-tolylphosphino-1,1'-binaphthyl | HCID 18398271 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-{4-[2-(3,4-Dimethyl-phenyl)-ethyl]phenylamino)-5-nitrobenzoic acid methyl ester | HCID 54139914 | 87.8% |
Reaction Steps
The title compound was prepared from 4-[2-(3,4-dimethylphenyl)ethyl]-benzenamine (1.0 g, 4.43 mmol), 2-bromo-5-nitrobenzoic acid methyl ester (0.96 g, 3.69 mmol), cesium carbonate (1.68 g, 5.17 mmol), tris(dibenzylideneacetone-dipaladium(0) (101 mg, 0.11 mmol) and (S)-(2,2′-bis(di-p-tolylphosphino-1,1′-binaphthyl (98%, (S)-tol-BINAP) (113 mg, 0.17 mmol) (Ligand/Pd=1.5) in anhydrous toluene (32 mL) using the procedure described in Example 2, step C. This procedure yielded an yellow solid, 1.31 g (3.24 mmol, 73%) of the desired product. mp 115-117° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06972287B1 |
| Source dataset | uspto-grants-2005_12 |
| ORD ID | ord-29762f8125c9414e9b2f781c10b073b5 |
| Source note | uspto-grants-2005_12 |