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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 880665Generated: October 30, 2026

Potassium tert-butoxide → N-[2-Chloro-4-(6-fluoro-3,4-dihydro-1H-isoquinolin-2-yl)-6-trifluoromethyl-phenyl]-3-cyclopentyl propionamide

https://huagongshe.com/reaction/880665

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium tert-butoxideHCID 23665647—
Reactant6-Fluoro-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 45074042—
ReactantN-(4-Bromo-2-chloro-6-trifluoromethyl-phenyl)-3-cyclopentyl propionamideHCID 58097325—
SolventTolueneHCID 1140—
ProductN-[2-Chloro-4-(6-fluoro-3,4-dihydro-1H-isoquinolin-2-yl)-6-trifluoromethyl-phenyl]-3-cyclopentyl propionamideHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08993593B2
Source datasetuspto-grants-2015_03
ORD IDord-be25831e989e4c23b73a79ac9a66f119
Source noteuspto-grants-2015_03