HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium tert-butoxide → N-[2-Chloro-4-(6-fluoro-3,4-dihydro-1H-isoquinolin-2-yl)-6-trifluoromethyl-phenyl]-3-cyclopentyl propionamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 6-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride | HCID 45074042 | — |
| Reactant | N-(4-Bromo-2-chloro-6-trifluoromethyl-phenyl)-3-cyclopentyl propionamide | HCID 58097325 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | N-[2-Chloro-4-(6-fluoro-3,4-dihydro-1H-isoquinolin-2-yl)-6-trifluoromethyl-phenyl]-3-cyclopentyl propionamide | HCID 24937077 | — |
Reaction Steps
Bis(dibenzylidineacetone)palladium (2 mg, 0.0035 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (3.3 mg, 0.0084 mmol) were added to dry toluene (10 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (140 mg, 1.25 mmol), 6-fluoro-1,2,3,4-tetrahydroisoquinoline hydrochloride salt (150 mg, 0.8 mmol) and N-(4-Bromo-2-chloro-6-trifluoromethyl-phenyl)-3-cyclopentyl-propionamide (200 mg, 0.5 mmol) were then added and the reaction mixture was stirred at 90° C. overnight. The reaction mixture was then cooled to room temperature; concentrated, and purified by thin layer chromatography (dichloromethane:methanol 5%) to afford the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08993593B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-be25831e989e4c23b73a79ac9a66f119 |
| Source note | uspto-grants-2015_03 |