Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Bromoisoquinoline | HCID 73743 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | Tert-butyl 2-amino-4-phenethylbenzoate | HCID 58508624 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68957320 | HCID 68957320 | 40.4% |
Reaction Steps
To toluene 1.0 mL solution of 4-bromoisoquinoline 0.12 g were added 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9.5 mg, tert-butyl 2-amino-4-phenethylbenzoate 59 mg, cesium carbonate 0.13 g, palladium acetate 0.90 mg and tris(dibenzylideneacetone)dipalladium(0) 3.7 mg at room temperature, and it was heated and refluxed for 7 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/L hydrochloric acid were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution sequentially, and the solvent was removed under reduced pressure. Ethyl acetate and hexane were added to the obtained residue, and solid matter was filtrated to give tert-butyl 2-((isoquinolin-4-yl)amino)-4-phenethylbenzoate 34 mg of a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08327467B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-1118cad789fc42df9ef96d4d59487760 |
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| Source note | uspto-grants-2012_12 |
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