Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Bromoisoquinoline | HCID 73743 | — |
| Reactant | Benzophenone imine | HCID 136809 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86676324 | HCID 86676324 | 58% |
Reaction Steps
In a 250 mL round flask 4-bromoisoquinoline (1 g, 4.81 mmol), benzophenone imine (2.41 mL, 14.42 mL), Pd(OAc)2 (33 mg, 0.14 mmol), BINAP (299 mg, 0.05 mmol), DPPF (266 g, 0.05 mmol) and triethylamine (0.17 mL, 1.20 mmol) were concentrated in vacuum for 15 min and then dissolved in 50 mL anhydrous toluene at room temperature for 20 min. Cs2CO3 (2.35 g, 7.21 mmol) was added to the reaction mixture. The reaction mixture was heated at 110° C. for 18 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure to afford the crude which was purified by column chromatography to give N-(diphenylmethylene)-isoquinolin-4-amine (853 mg, 58%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09029378B2 |
|---|
| Source dataset | uspto-grants-2015_05 |
|---|
| ORD ID | ord-b67cb7385d8e4a07a562fb828f0b970c |
|---|
| Source note | uspto-grants-2015_05 |
|---|
